Sagar, B. K. and Yathirajan, H. S. and Rathore, Ravindranath S. and Glidewell, Christopher (2018) Synthesis and structures of six closely related \it N-3-(2-chloro{\-}benzo{\-}yl)-5-ethyl{\-}thio{\-}phen-2-ylaryl{\-}amides, together with an isolated reaction inter{\-}mediate: order {\it versus} disorder, mol{\-}ecular conformations and hydrogen bonding in zero, one and two dimensions. Acta Crystallographica Section C, 74 (2). pp. 203-211.
Full text not available from this repository. (Request a copy)Abstract
Six closely related N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]arylamides have been synthesized and structurally characterized, together with a representative reaction intermediate. In each of N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]benzamide, C20H16ClNO2S, (I), N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐4‐phenylbenzamide, C26H20ClNO2S, (II), and 2‐bromo‐N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]benzamide, C20H15BrClNO2S, (III), the molecules are disordered over two sets of atomic sites, with occupancies of 0.894 (8) and 0.106 (8) in (I), 0.832 (5) and 0.168 (5) in (II), and 0.7006 (12) and 0.2994 (12) in (III). In each of N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐2‐iodobenzamide, C20H15ClINO2S, (IV), and N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐2‐methoxybenzamide, C21H18ClNO3S, (V), the molecules are fully ordered, but in N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐2,6‐difluorobenzamide, C20H14ClF2NO2S, (VI), which crystallizes with Z′ = 2 in the space group C2/c, one of the two independent molecules is fully ordered, while the other is disordered over two sets of atomic sites having occupancies of 0.916 (3) and 0.084 (3). All of the molecules in compounds (I)–(VI) exhibit an intramolecular N—H…O hydrogen bond. The molecules of (I) and (VI) are linked by C—H…O hydrogen bonds to form finite zero‐dimensional dimers, which are cyclic in (I) and acyclic in (VI), those of (III) are linked by C—H…π(arene) hydrogen bonds to form simple chains, and those of (IV) and (V) are linked into different types of chains of rings, built in each case from a combination of C—H…O and C—H…π(arene) hydrogen bonds. Two C—H…O hydrogen bonds link the molecules of (II) into sheets containing three types of ring. In benzotriazol‐1‐yl 3,4‐dimethoxybenzoate, C15H13N3O4, (VII), the benzoate component is planar and makes a dihedral angle of 84.51 (6)° with the benzotriazole unit. Comparisons are made with related compounds.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | synthesis, thiophene derivatives, amides, reaction mechanism, crystal structure, disorder, molecular conformation, hydrogen bonding, supramolecular assembly |
| Subjects: | C Chemical Science > Chemistry |
| Divisions: | Department of > Chemistry |
| Depositing User: | Manjula P Library Assistant |
| Date Deposited: | 08 Aug 2019 09:31 |
| Last Modified: | 08 Aug 2019 09:32 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/6244 |
Actions (login required)
 |
View Item |
