Synthesis Crystal Structure and Spectral Properties of New Sulfonamides

Abstract

Abstract: In this paper, we report new sulfonamide derivatives, 4-((2,4-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid (1), ethyl 4-((naphthalene-2-sulfonamido)methyl)cyclohexanecarboxylate (2), and ethyl 4-((2,5-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylate (3). The compounds were and characterized by FTIR, ESI-MS, and X-ray crystallography. Single crystal X-ray diffraction analysis shows that 1 crystallizes in the orthorhombic space group Pbcn, 2 in the monoclinic space group Cc and 3 in the monoclinic space group Cc. All three molecules feature hydrogen bonding. Graphical Abstract: Three sulfonamide derivatives, 4-((2,4-dichlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid (1), ethyl 4-((naphthalene-2-sulfonamido)methyl)cyclohexanecarboxylate (2) and ethyl 4-((2,5-dichlorophenylsulfonamido) methyl)cyclo-hexanecarboxylate (3) have been synthesized and their structures confirmed by single crystal X-ray diffraction. Hydrogen bonding in compound 1 involves carboxylic groups and N–H moieties as well as non-classical C–H···O interactions, while in 2 and 3, the N–H moiety and an oxygen atom of the sulfonamide functional group of neighboring molecules are involved. [Figure not available: see fulltext.]