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Mycopan is a genus established for Hydropus scabripes by Redhead, Moncalvo & Vilgalys (in Redhead 2013). They considered the genus to be distinct based on morphology and the phylogenetic analysis by Moncalvo et al. (2002) which included a sequence of Hydropus scabripes (AF042635, DAOM 192847) unrelated to the type species of Hydropus (H. fuliginarius). Subsequent sequences of material identified as Hydropus scabripes are not conspecific with the sequence of DAOM 192847. We consider this sequence (obtained from a mycelium culture) to be misidentified. We investigated the true phylogenetic position of authentic Mycopan including genera previously included in Cyphellaceae and Porotheleaceae. Sixteen collections of M. scabripes from Europe and North America were studied on morphological and molecular basis (nrITS and nrLSU sequences). No sequences were obtained from the holotype of Mycopan scabripes, and we designate an epitype to fix the interpretation of this species and the genus Mycopan. Mycopan is maintained as a good genus nested within Cyphellaceae as sister to the mycenoid genus Atheniella. The misidentified Hydropus scabripes AF042635 (DAOM 192847) represents a different species that is closely related to the holotype (and a new Italian collection) of Hebelomina microspora and the monospecific genus Pleurella described from New Zealand. Consequently, Hebelomina microspora is transferred to the emended genus Pleurella, which is sister to Baeospora within the Cyphellaceae. Additionally, based on these phylogenetic results, an updated taxonomic arrangement of Cyphellaceae and Porotheleaceae is proposed, emphasizing once again the polyphyletic nature of Hydropus and Gerronema.

A new classification of the taxa formerly ascribed to Biannulariaceae (≡ Catathelasmataceae), viz. Catathelasma (type), Callistosporium, Pleurocollybia, Macrocybe, Pseudolaccaria, Guyanagarika and Anupama is here proposed. Phylogenetic inference of the Tricholomatineae based on the analysis of a combined dataset of nuclear genes including ITS, 18S and 28S rDNA, tef1 and rpb2 data supports significantly a monophyletic origin of the aforementioned genera with the exception of Catathelasma, which is significantly related with Bonomyces and Cleistocybe. Biannulariaceae is therefore emended to include the clade formed by Catathelasma, Bonomyces and Cleistocybe. Consequently, the new family Callistosporiaceae is proposed to name the clade containing Callistosporium (= Pleurocollybia) and related genera. Species of Callistosporium with distant lamellae, long hygrophoroid basidia and large amygdaliform spores are accommodated in the new genus Xerophorus. Finally, the new species Callistosporium pseudofelleum and Macrocybe sardoa are described, Clitocybe hesleri and C. fellea are combined into Callistosporium and Pseudolaccaria, respectively, and Callistosporium olivascens var. donadinii is upgraded to species rank and combined into Xerophorus.

The reaction rates for the nucleophilic aromatic substitution of 4,6-dichloro-5-nitrobenzofuroxan 1 with eight aliphatic amines (characterized by very different basicities/ nucleophilicities) and three anilines have been measured in both methanol and toluene. The obtained rates have been related to the basicity (pKaH in water and Kb in benzene) or nucleophilicity (N Mayr constants) of the tested amines. The whole of the obtained kinetic data has furnished useful information on the high nucleophilic reactivity of benzofuroxan derivatives, which has been related essentially to two factors: the high electron-drawing ability/power of the condensed furoxan ring and the low aromatic character of the benzofuroxan system.

A new classification of several clitocyboid taxa is here proposed to accommodate results from multigenic phylogenetic inference. The analysis of ITS rDNA as well as a combined dataset including 18S and 28S rDNA, tef1 and rpb2 data, support significantly a shared monophyletic origin of the genera Pseudoclitocybe, Musumecia and Pogonoloma, and the species Clitocybe alexandri and C. harperi. The new family Pseudoclitocybaceae is here proposed to name this clade, characterized by the presence of loop-like clamp connections in most species, absence of cystidia, and parallel hymenophoral trama with broad, cylindrical hyphae with intracellular granulations. The new genera Clitopaxillus and Harmajaea are proposed to accommodate the type species C. alexandri and H. harperi, as well as the combination H. wellsiae. In addition, two new species are described: C. fibulatus has a differential distribution of clamp connections in the basidiome, while H. guldeniae is, by now, an exclusively European taxon with brownish pileus, somewhat decurrent gills, ovoid spores and basidia longer than those of H. harperi. Finally, the species concept within Pseudoclitocybe and Pogonoloma is discussed and descriptions of the most representative species are provided.

Nomenclatural type definitions are one of the most important concepts in biological nomenclature. Being physical objects that can be re-studied by other researchers, types permanently link taxonomy (an artificial agreement to classify biological diversity) with nomenclature (an artificial agreement to name biological diversity). Two proposals to amend the International Code of Nomenclature for algae, fungi, and plants (ICN), allowing DNA sequences alone (of any region and extent) to serve as types of taxon names for voucherless fungi (mainly putative taxa from environmental DNA sequences), have been submitted to be voted on at the 11th International Mycological Congress (Puerto Rico, July 2018). We consider various genetic processes affecting the distribution of alleles among taxa and find that alleles may not consistently and uniquely represent the species within which they are contained. Should the proposals be accepted, the meaning of nomenclatural types would change in a fundamental way from physical objects as sources of data to the data themselves. Such changes are conducive to irreproducible science, the potential typification on artefactual data, and massive creation of names with low information content, ultimately causing nomenclatural instability and unnecessary work for future researchers that would stall future explorations of fungal diversity. We conclude that the acceptance of DNA sequences alone as types of names of taxa, under the terms used in the current proposals, is unnecessary and would not solve the problem of naming putative taxa known only from DNA sequences in a scientifically defensible way. As an alternative, we highlight the use of formulas for naming putative taxa (candidate taxa) that do not require any modification of the ICN. Publisher’s Note A first version of this text was prepared by the first eight authors and the last one, given here. The other listed co-authors in the article PDF support the content, and their actual contributions varied from only support to additions that substantially improved the content. The full details of all co-authors, with their affiliations, are included in Supplementary Table 1 after p.175 of the article for reasons of clarity and space. Slavomír Adamčík Institute of Botany, Plant Science and Biodiversity Centre, Slovak Academy of Sciences, Dúbravská cesta 9, 845 23 Bratislava, Slovakia Teuvo Ahti Finnish Museum of Natural History, P.O. Box 7, 00014 University of Helsinki, Finland M. Catherine Aime Purdue University, 915 W. State St., West Lafayette, Indiana 47907, U.S.A. A. Martyn Ainsworth Royal Botanic Gardens, Kew, Richmond, Surrey, TW9 3AB, United Kingdom László Albert Hungarian Mycological Society, 1087 Könyves Kálmán krt. 40, Budapest, Hungary Edgardo Albertó Instituto de Investigaciones Biotecnológicas-Instituto Tecnológico de Chascomús, Universidad Nacional de San Martin-Consejo Nacional de Investigaciones Científicas y Técnicas, Buenos Aires, Argentina Alberto Altés García Facultad de Biología, Ciencias Ambientales y Química, Universidad de Alcalá, 28805 Alcalá de Henares, Madrid, Spain Dmitry Ageev SIGNATEC Ltd., 630090, Novosibirsk, Akademgorodok (Novosibirsk Scientific Center), Inzhenernaya str., 22, Russia Reinhard Agerer Ludwig-Maximilians-Universität München, Menzinger Str. 67, 80638 München, Germany Begona Aguirre-Hudson Royal Botanic Gardens, Kew, Richmond, Surrey, TW9 3AB, United Kingdom Joe Ammirati University of Washington, Seattle, Washington 98195-1800, U.S.A. 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Moscoso, Apartado 21-9, Santo Domingo, Dominican Republic Vladimír Antonín Moravian Museum, Zeny trh 6, 659 37 Brno, Czech Republic Takayuki Aoki Genetic Resources Center, National Agriculture and Food Research Organization, 2-1-2 Kannondai, Tsukuba, Ibaraki 305-8602, Japan André Aptroot ABL Herbarium, G.v.d.Veenstraat 107, 3762 XK Soest, The Netherlands Didier Argaud 40 rue du Justemont, 57290 Fameck, France Blanca Imelda Arguello Sosa Instituto Tecnológico de Ciudad Victoria, Tecnológico Nacional de México, Ciudad Victoria, Tamaulipas, Mexico Arne Aronsen Torødveien 54, 3135 Torød, Norway Ulf Arup Biological Museum, Lund University, Box 117, 221 00 Lund, Sweden Bita Asgari Iranian Research Institute of Plant Protection, Agricultural Research, Education and Extension Organization, Tehran, Iran Boris Assyov Institute of Biodiversity and Ecosystem Research, Bulgarian Academy of Sciences, 2 Gagarin Str., 1113 Sofia, Bulgaria Violeta Atienza Facultad de Ciencias Biológicas, Universitat de València, C/Dr Moliner 50, 46100, Burjasot, Valencia, Spain Ditte Bandini Panoramastr 47, 69257 Wiesenbach, Germany João Luís Baptista-Ferreira Instituto de Biossistemas e Ciências Integrativas, Faculdade de Ciências da Universidade de Lisboa, 1749-016 Lisboa, Portugal Hans-Otto Baral Blaihofstr. 42, 72074 Tübingen, Germany Tim Baroni The State University of New York, 340 Bowers Hall, P.O. 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Zhurbenko Komarov Botanical Institute of the Russian Academy of Sciences, 2 Prof. Popov Street, St. Petersburg, 197376, Russia The following institutions are also supporting the present text (institutional support means that committees from the mentioned) Asociación Micológica Carlos Spegazzini (Argentina) Austrian Mycological Society (Austria) Croatian Mycological Society (Croatia) Committee of the Czech Scientific Society for Mycology (Czech Republic) The Netherlands Mycological Society (The Netherlands) Sociedad Española de Liquenología (Portugal/Spain) Iberian Mycological Society (which is under constitution, Portugal/Spain) Federación de Asociaciones Micológicas Andaluzas (FAMA) (Spain) Asociación Botánica y Micológica de Jaén (Spain) Asociación Micológica Hispalense Muscaria (Spain) Societat Micològica Valenciana (Spain)

A molecular multigene analysis (ITS, 18S and 28S nrLSU ribosomal DNA, tef1, rpb2) was used to support the proposition of three new genera of clitocyboid fungi. Leucocybe is proposed to accommodate the clade formed by Clitocybe connata and C. candicans. Clitocybe inornata is invested as type species of Atractosporocybe, while the new genus, Rhizocybe, is proposed for the former species of section Vernae of Clitocybe, C. vermicularis, C. pruinosa and C. rhizoides. The three lineages are related to the families Lyophyllaceae and Entolomataceae and independent from the Clitocybeae clade. Morphologically Rhizocybe is characterized by the presence of conspicuous rhizomorphs, while Atractosporocybe presents long fusiform spores. Leucocybe includes two whitish species in the former section Candicantes of Clitocybe, but no relevant shared characteristic feature was detected. Other whitish clitocyboid species, such as C. phyllophila (= C. cerussata), C. dealbata, C. rivulosa, and Singerocybe hydrogramma, are shown to be genetically related to the core lineage of the Clitocybeae.

Several collections of Amanita species from section Vaginatae have been reported to be strictly associated with Helianthemum plants growing in grasslands, a still largely under-explored ectomycorrhizal habitat. The main aim of this study was to investigate the taxonomic status and phylogenetic position of strictly Helianthemum -associated Amanita sect. Vaginatae taxa, informally named Amanita “ helianthemicola ” . Collections from Italy, England and France were included in this study. The morphologically closely related species complex A. lividopallescens was also examined. Analyses were carried out based on both morphological and molecular data (phylogenetic analysis of the nrITS sequences). All investigated Amanita collections, which are strictly associated with Helianthemum nummularium, turned out to be conspecific with A . simulans. Amanita simulans was recently described from Sardinia (Italy) from Populus nigra habitats based on morphological characters only. As the holotype of A. simulans was lost, a neotype is designated here based on a voucher from the original collecting area. Amanita simulans is re-described, and an extensive discussion on the morphological variability, host species range, distribution and related taxa is provided. Amanita lividopallescens was confirmed as a good species, and re-delimited based on our phylogenetic analysis; moreover, it was epitypified with a recent and well-documented collection from Corse (France) . Amanita stenospora is a synonym of A . lividopallescens, being a colour form of the latter without taxonomic value.

Pseudoporpoloma ( Agaricales ) is a new monospecific genus established for Agaricus pes-caprae, a grassland species previously placed in Tricholoma or Porpoloma . Pseudoporpoloma is morphologically distinguished by a Tricholoma -like habit, a conical radially fibrillose pileus, and amyloid spores. Phylogenetic analyses based on a combined ITS-LSU- rpb2 sequence dataset place Pseudoporpoloma close to Pseudotricholoma and Tricholoma .

International audience; This paper is a compilation of notes on 142 fungal taxa, including five new families, 20 new genera, and 100 new species, representing a wide taxonomic and geographic range. The new families, Ascocylindricaceae, Caryosporaceae and Wicklowiaceae (Ascomycota) are introduced based on their distinct lineages and unique morphology. The new Dothideomycete genera Pseudomassariosphaeria (Amniculicolaceae), Heracleicola, Neodidymella and Pseudomicrosphaeriopsis (Didymellaceae), Pseudopithomyces (Didymosphaeriaceae), Brunneoclavispora, Neolophiostoma and Sulcosporium (Halotthiaceae), Lophiohelichrysum (Lophiostomataceae), Galliicola, Populocrescentia and Vagicola (Phaeosphaeriaceae), Ascocylindrica (Ascocylindricaceae), Elongatopedicellata (Roussoellaceae), Pseudoasteromassaria (Latoruaceae) and Pseudomonodictys (Macrodiplodiopsidaceae) are introduced. The newly described species of Dothideomycetes (Ascomycota) are Pseudomassariosphaeria bromicola (Amniculicolaceae), Flammeascoma lignicola (Anteagloniaceae), Ascocylindrica marina (Ascocylindricaceae), Lembosia xyliae (Asterinaceae), Diplodia crataegicola and Diplodia galiicola (Botryosphaeriaceae), Caryospora aquatica (Caryosporaceae), Heracleicola premilcurensis and Neodidymella thailandicum (Didymellaceae), Pseudopithomyces palmicola (Didymosphaeriaceae), Floricola viticola (Floricolaceae), Brunneoclavispora bambusae, Neolophiostoma pigmentatum and Sulcosporium thailandica (Halotthiaceae), Pseudoasteromassaria fagi (Latoruaceae), Keissleriella dactylidicola (Lentitheciaceae), Lophiohelichrysum helichrysi (Lophiostomataceae), Aquasubmersa japonica (Lophiotremataceae), Pseudomonodictys tectonae (Macrodiplodiopsidaceae), Microthyrium buxicola and Tumidispora shoreae (Microthyriaceae), Alloleptosphaeria clematidis, Allophaeosphaeria cytisi, Allophaeosphaeria subcylindrospora, Dematiopleospora luzulae, Entodesmium artemisiae, Galiicola pseudophaeosphaeria, Loratospora luzulae, Nodulosphaeria senecionis, Ophiosphaerella aquaticus, Populocrescentia forlicesenensis and Vagicola vagans (Phaeosphaeriaceae), Elongatopedicellata lignicola, Roussoella magnatum and Roussoella angustior (Roussoellaceae) and Shrungabeeja longiappendiculata (Tetraploasphaeriaceae). The new combinations Pseudomassariosphaeria grandispora, Austropleospora archidendri, Pseudopithomyces chartarum, Pseudopithomyces maydicus, Pseudopithomyces sacchari, Vagicola vagans, Punctulariopsis cremeoalbida and Punctulariopsis efibulata Dothideomycetes. The new genera Dictyosporella (Annulatascaceae), and Tinhaudeus (Halosphaeriaceae) are introduced in Sordariomycetes (Ascomycota) while Dictyosporella aquatica (Annulatascaceae), Chaetosphaeria rivularia (Chaetosphaeriaceae), Beauveria gryllotalpidicola and Beauveria loeiensis (Cordycipitaceae), Seimatosporium sorbi and Seimatosporium pseudorosarum (Discosiaceae), Colletotrichum aciculare, Colletotrichum fusiforme and Colletotrichum hymenocallidicola (Glomerellaceae), Tinhaudeus formosanus (Halosphaeriaceae), Pestalotiopsis subshorea and Pestalotiopsis dracaenea (Pestalotiopsiceae), Phaeoacremonium tectonae (Togniniaceae), Cytospora parasitica and Cytospora tanaitica (Valsaceae), Annulohypoxylon palmicola, Biscogniauxia effusae and Nemania fusoideis (Xylariaceae) are introduced as novel species to order Sordariomycetes. The newly described species of Eurotiomycetes are Mycocalicium hyaloparvicellulum (Mycocaliciaceae). Acarospora septentrionalis and Acarospora castaneocarpa (Acarosporaceae), Chapsa multicarpa and Fissurina carassensis (Graphidaceae), Sticta fuscotomentosa and Sticta subfilicinella (Lobariaceae) are newly introduced in class Lecanoromycetes. In class Pezizomycetes, Helvella pseudolacunosa and Helvella rugosa (Helvellaceae) are introduced as new species. The new families, Dendrominiaceae and Neoantrodiellaceae (Basidiomycota) are introduced together with a new genus Neoantrodiella (Neoantrodiellaceae), here based on both morphology coupled with molecular data. In the class Agaricomycetes, Agaricus pseudolangei, Agaricus haematinus, Agaricus atrodiscus and Agaricus exilissimus (Agaricaceae), Amanita melleialba, Amanita pseudosychnopyramis and Amanita subparvipantherina (Amanitaceae), Entoloma calabrum, Cora barbulata, Dictyonema gomezianum and Inocybe granulosa (Inocybaceae), Xerocomellus sarnarii (Boletaceae), Cantharellus eucalyptorum, Cantharellus nigrescens, Cantharellus tricolor and Cantharellus variabilicolor (Cantharellaceae), Cortinarius alboamarescens, Cortinarius brunneoalbus, Cortinarius ochroamarus, Cortinarius putorius and Cortinarius seidlii (Cortinariaceae), Hymenochaete micropora and Hymenochaete subporioides (Hymenochaetaceae), Xylodon ramicida (Schizoporaceae), Colospora andalasii (Polyporaceae), Russula guangxiensis and Russula hakkae (Russulaceae), Tremella dirinariae, Tremella graphidis and Tremella pyrenulae (Tremellaceae) are introduced. Four new combinations Neoantrodiella gypsea, Neoantrodiella thujae (Neoantrodiellaceae), Punctulariopsis cremeoalbida, Punctulariopsis efibulata (Punctulariaceae) are also introduced here for the division Basidiomycota. Furthermore Absidia caatinguensis, Absidia koreana and Gongronella koreana (Cunninghamellaceae), Mortierella pisiformis and Mortierella formosana (Mortierellaceae) are newly introduced in the Zygomycota, while Neocallimastix cameroonii and Piromyces irregularis (Neocallimastigaceae) are introduced in the Neocallimastigomycota. Reference specimens or changes in classification and notes are provided for Alternaria ethzedia, Cucurbitaria ephedricola, Austropleospora, Austropleospora archidendri, Byssosphaeria rhodomphala, Lophiostoma caulium, Pseudopithomyces maydicus, Massariosphaeria, Neomassariosphaeria and Pestalotiopsis montellica.

linear free energy ortho-correlations The kinetics of SNAr reactions of some 2-bromo-3-X-5-nitrothiophenes (X = Me, H, Br, CONH2, CO2Me, COMe, SO2Me, CN and NO2) with some primary (n-butylamine and benzylamine) and secondary (pyrrolidine, piperidine, morpholine and N-benzylamine) amines have been measured in benzene as a function of nucleophile concentration. Most of the reactions studied show apparent kinetic constants little affected or not affected by an increase in amine concentration, indicating that the overall reaction rate is controlled by the formation of the reaction intermediate. The reactions of the substrates where X = Br and CN with the two primary amines proved to be base-catalysed. The k3B/k-1values calculated for these substituents are inconsistent with the hypothesis of a base catalysis for the intermediate decomposition and strongly suggest a catalysis of the first step of the reaction pathway.

The rate constants of the title reactions have been measured in benzene at 20 °C. The reactions with benzylamine are not base-catalysed. The second-order kinetic constant for the reactions with N-benzylmethylamine, with the exception of the unsubstituted compound (X = H), increases in a hyperbolical way with increasing nucleophile concentration. A non-linear regression treatment of kinetic data allows the calculation of k1 and k3B/k–1 for each catalysed system. k3B/k–1 is not a monotonic function of the X substituent. This result has been rationalised on the grounds of a specific base–general acid (SB–GA) mechanism for the base catalysis.

A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k(CONH)()2/k(CO)()2(Me) 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (k(CONH)()2/k(CO)()2(Me) 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol k(CONH)()2/k(CO)()2(Me) ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.

The kinetics of the reactions of some 2-L-3-Y-5-nitrothiophenes (L = Br, OC6H5, OC6H4NO2-p YCONH2, CO2Me) with n-butylamine, benzylamine, pyrrolidine and piperidine in benzene at 293.15 K have been studied with the aim of obtaining and insight into the role played by the ortho-like substituent (Y) in determining the occurrence and the form of base catalysis. The results obtained have also allowed to gain important information about the interactions between the substituents, the thiophene ring and the reaction centre.

Based on a combined ITS-LSU rDNA analysis, the omphalinoid genus Haasiella is shown to be part of the Hygrophoroid clade and sister to Hygrophorus. H. venustissima and H. splendidissima are conspecific; H. splendidissima is the tetrasporic/clamped and heterothallic form of H. venustissima.

The apparent pseudo-first-order rate constants for the title reaction give a curvilinear plot versus tertiary amine concentration, according to the equation kA  (ku, + K1k2[TEA])/(1 + K1[TEA]). This shows the occurrence of two different reaction pathways; the one, independent of [TEA] and the other, dependent on [TEA], which involves a fast conversion of the substrate into an acid-base adduct or an ion pair followed by its slow conversion into the corresponding triazole. The substituent effects on these reactions have also been studied.

La formation d'une liaison carbone-carbone dans un heterocycle deficient en electrons Π peut s' effectuer par deux methodes en deux etapes qui sont examinees :addition d'un heterocycle avec un organometallique suivie soit d'une deshydrogenation soit de reactions croisees de couplage

In the framework of studies concerning the effect of the structure of the side chain on the mechanism and the reactivity in mononuclear heterocyclic rearrangements, the reactivity of some N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-arylformamidines 3 in dioxane–water in the pS+-range 6.0–15.0 was studied and compared with that of arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole 7 and of 3-arylureido-5-phenyl-1,2,4-oxadiazoles 5. A plot of the logarithms of the rate constants versus pS+showed the occurrence of an uncatalysed (pS+-independent) and of a catalysed (pS+-dependent and then pS+-independent) range. Kinetic data pointed out that the base catalysis is specific, in accord with the relatively high acidity of the formamidines used. The substituent effects on the reactivity were compared with those observed in other mononuclear heterocyclic rearrangements.

Chelation-controlled, palladium-catalyzed arylation of vinyl ethers with nitrogen-containing directing groups has been studied. Ethenyloxyalkylamines 1a-c and pyridines 2a-d, representing different ...

The protonation of some 5-substituted 3-nitro-2-pyrrolidin-1-ylthiophenes 1C and 3-substituted 5-nitro-2-pyrrolidin-1-ylthiophenes 2C in aqueous perchloric acid has been studied. The modified Hammett, Bunnett–Olsen and Marziano–Cox–Yates methods have been used to calculate pKBH+ values, which have been correlated with substituent effects. Furthermore, the protonation of pyrrolidin-1-ylthiophenes 1C and 2C has been compared with that of the corresponding N,N-di-methylamino-(1A and 2A) and piperidin-1-yl-thiophenes (1B and 2B). The results have been interpreted on the grounds of the different interactions occurring between the amino group at C-2 and the nitro group or variable substituent at C-3.

A 13C NMR study has been carried out in (CD3)2SO on the thiophene derivatives 5 and 7 and the related Meisenheimer adducts 6 and 8. The data obtained, and in particular the sums of the chemical-shift changes (ΣΔδ) at C-3, C-4 and C-5, accompanying the formation of the adducts, are compared with the corresponding data previously obtained for analogous substrates 1 and 3 and adducts 2 and 4. The four series of ΣΔδ values are then examined in the light of the already reported thermodynamic (Ke) and kinetic (k1) constants for the formation of the adducts. For a given X-substituent, log Ke values increase linearly as the corresponding absolute ΣΔδ values decrease. On these grounds, the smaller π-electron-density rearrangement accompanying the formation of gem-dimethoxy adducts emerges as an important factor, contributing to the larger observed Ke values. A further outcome is that, within a single series of adducts, a linear relationship of either log Ke or log k1 with Δδ holds only when excluding the terms with X = Ac or NO2. Such findings are interpreted on the basis of the two-component nature of the substituent –R effects: while for the nitro and the acetyl substituents the π-electron acceptor component is prevalent, the stabilizing effect of the other substituents is due mainly to a charge–dipole interaction. The analysis of some literature data for the benzene series fits the above conclusions.

The apparent pseudo-first-order rate constants for the title reaction give a curvilinear plot versus tertiary amine concentration, according to the equation kA  (ku, + K1k2[TEA])/(1 + K1[TEA]). This shows the occurrence of two different reaction pathways; the one, independent of [TEA] and the other, dependent on [TEA], which involves a fast conversion of the substrate into an acid-base adduct or an ion pair followed by its slow conversion into the corresponding triazole. The substituent effects on these reactions have also been studied.

The synthetically useful nucleophilic attack on nitrobenzo-[b]thiophenes, a starting point for ring-opening/ring-closure pathways to different heterocyclic systems, has been investigated in detail. 3-Nitrobenzo[b]thiophene (9) and 2-nitrob-enzo[b]thiophene (10) react with sodium methoxide in either DMSO or methanol to give the relevant "Meisenheimer-type" adducts 9' and 10', identified by NMR spectroscopy. A UV study indicated that the equilibrium constants for the formation of 9' at 293 K are 10.1 and 40700 L mol -1 in methanol and in DMSO, respectively. Competition reactions showed that the stability constant of 10' is lower than that of 9': accordingly, DFT [B3LYP/6-31+G(d,p)] calculations indicate that the formation of 9' is thermodynamically more favoured than that of 10' both in the gas phase and in DMSO. The reason for the opposite sequence in the stability constants previously found for the corresponding gem-dimethoxy Meisenheimer adducts 7' and 8' was therefore investigated in depth and appears to be a consequence of different steric interactions in the starting compounds, 2-methoxy-3-nitro-(7) and 3-methoxy-2-nitrobenzo[b]thiophene (8), respectively. A study of 13 C NMR chemical shift changes accompanying the formation of adducts 9' and 10' confirms that the formation of the adduct exhibiting the larger stability constant is accompanied by a smaller π electron density redistribution, as we have previously found in other cases all governed by electronic effects. The opposite behaviour is observed in the formation of the gem-dimethoxy adducts 7' and 8', which is a consequence of the predominance of steric effects. Further outcomes of more general interest deal with the aromatic character of benzo[b]thiophenes. NMR spectroscopic data and calculated bond lengths show that in the studied reactions the benzene ring, unlike the thiophene one, is scarcely affected by methoxide addition, retaining its nearly "full" aromatic character. Benzocondensation increases the stability constants of σ-adducts mainly because of a marked reduction in the aromatic character of the thiophene ring in the substrates.

The kinetics of the title reaction has been studied in methanol as a function of amine and methoxide ion concentrations. The kinetic coefficients obtained point out that the reaction is catalysed by methoxide through a SB catalysis mechanism.