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A survey of supramolecular association involving the oxide-O atom in the crystals of triorganoamine N-oxide derivatives, RR′R″N(+)O(−).
- Source :
-
Zeitschrift für Kristallographie. Crystalline Materials . Mar2024, Vol. 239 Issue 3/4, p67-92. 26p. - Publication Year :
- 2024
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Abstract
- Trimethylamine N-oxide, Me3N(+)O(−), is an important molecule in biology and medicine. Herein, a survey of the interactions involving the oxide-O atom in crystals containing derivatives of Me3N(+)O(−), namely RR′R″N(+)O(−), is presented; R,R′, R″ = alkyl and/or aryl. A total of 119 RR′R″N(+)O(−) molecules were analysed for the supramolecular interactions involving the oxide-O atom. Hydrates form the largest class of crystals, comprising over 40 % of the 91 crystals investigated, a value slightly higher than expectation. Over 80 % of molecules had at least one O–H⋯O(−)(oxide) hydrogen bond: 3, 45 and 33 % of all molecules had three, two or one O–H⋯O(−)(oxide) hydrogen bonds, respectively. Further, nearly 15 % of molecules formed at least one N–H⋯O(−)(oxide) hydrogen bond, sometimes operating in concert with O–H⋯O(−)(oxide) hydrogen bonds. The overwhelming majority of molecules featured inter- and/or intra-molecular supporting C–H⋯O(−)(oxide) contacts so that a diverse range of supramolecular interaction patterns is apparent, a situation made more complicated by the appearance of different supramolecular association patterns often observed for independent molecules in crystals with more than one molecule in the crystallographic asymmetric-unit. Of the 6 % of molecules devoid of conventional A–H⋯O(−)(oxide) hydrogen bonds, all formed three or four inter-/intra-molecular C–H⋯O(−)(oxide) contacts usually characterised by at least one short H⋯O(−)(oxide) distance. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 21944946
- Volume :
- 239
- Issue :
- 3/4
- Database :
- Academic Search Index
- Journal :
- Zeitschrift für Kristallographie. Crystalline Materials
- Publication Type :
- Academic Journal
- Accession number :
- 176508753
- Full Text :
- https://doi.org/10.1515/zkri-2024-0061