The formation of the first transition metal complexes of N-heterocyclic carbenes (NHCs) by ændash;fele and Wanzlick in 1968 and the discovery of the first stable and isolable free carbenes by Arduengo in 1991 fostered the growth of this fundamental area of chemical research. Currently, NHCs and their metal complexes are intensely studied for applications such as catalysis and most recently their pharmaceutical properties. The latter has shown promising results and thus will be the primary focus of this dissertation. In general, this dissertation will provide a description of the synthesis and antimicrobial properties of a novel class of silver NHC complexes derived from 4,5-dichloroimidazole and a comparison of its enhanced stability in relation to other silver NHCs synthesized in our laboratory. Chapter 1, the introduction, provides an overview of the medicinal applications of various metal NHC complexes including silver, gold, ruthenium, rhodium, and palladium. This follows a necessary discussion of the known properties of the metals including antimicrobial, antitumor, toxicity, resistance and proposed mechanisms of action. Chapter 2, discusses the synthesis, properties, and antimicrobial activity of a silver(I) acetate NHC complex derived from 4,5-dichloroimidazole with enhanced stability. This discussion is coupled with a comparison to two other structurally similar complexes lacking similar enhanced stability properties. Chapter 3 will provide a detailed account of the stability of the silver NHC complex reported in chapter 2 in various forms of aqueous media formulations including D2O, 0.9% NaCl/D2O, and broth/D2O mixtures utilizing NMR spectral techniques. Chapter 4 will focus on the synthesis of a silver NHC complex bearing a lipophilic substituent, its incorporation into L-tyrosine polyphosphate (LTP) nanospheres, and its in vivo antimicrobial efficacy when delivered to mice inoculated with Pseudomonas aeruginosa. Chapter 5 is devoted to the synthesis and characterization of imidazolium salt precursors functionalized with a variety of substituents and their corresponding silver NHC complexes. In chapter 6, the potential use of several different silver NHC complexes as a treatment of Onychomycosis, a common fungal infection of the nails is explored. The in vitro antifungal activity and penetration potential is reported.