Halogenated C,N-diarylacetamides: Molecular conformations and supramolecular assembly

Nayak, P. S. and Jasinski, J. P. and Golen, James A. and Narayana, B. and Kaur, M. and Yathirajan, H. S. and Glidewell, Christopher (2014) Halogenated C,N-diarylacetamides: Molecular conformations and supramolecular assembly. Acta Crystallographica Section C: Structural Chemistry, 70. pp. 889-894. ISSN 2053-2296

Text (Full Text) Che_2014_Kaur.pdf - Published Version Download (1MB)

Abstract

The structures of four halogenated N,2-diaryl­acetamides are reported and compared with a range of analogues. N-(4-Chloro-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14ClNO, (I), and N-(4-bromo-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14BrNO, (II), are isostructural in the space group P\overline{1}. The mol­ecules of (I) and (II) are linked into chains of rings by a combination of N-H...O and C-H...[pi](arene) hydrogen bonds. The mol­ecules of N-(4-chloro-3-methyl­phen­yl)-2-(2,4-di­chloro­phen­yl)acetamide, C15H12Cl3NO, (III), and N-(4-bromo-3-methyl­phen­yl)-2-(2-chloro­phen­yl)acetamide, C15H13BrClNO, (IV), are linked into simple C(4) chains by N-H...O hydrogen bonds, but significant C-H...[pi](arene) inter­actions are absent. The N-aryl groups in compounds (III) and (IV) adopt a different orientation, by ca 180°, from that of the corresponding groups in compounds (I) and (II), but otherwise the conformations of (I)-(IV) are very similar. Comparisons are drawn between compounds (I) and (IV) and a range of analogues of the type R1CH2CONHR2, where R2 represents a halogenated aryl ring and R1 represents either another halogenated aryl ring or a naphthalen-1-yl unit.

Item Type:	Article
Uncontrolled Keywords:	Crystal structure, Hydrogen bonds, Molecules, chemical structure, chemistry, Molecular Structure, Crystallography, hydrogen bond, Hydrogen Bonding, X ray crystallography, X-Ray, Chains, Conformations, Molecular conformation, Supramolecular assemblies, Supramolecular chemistry, Complexation, conformation, Molecular Conformation, Iodine, acetamide derivative, Acetamides, naphthalene derivative, Naphthalenes, O rings, acetamide, acetamides, Benzyl penicillins, C, halogenation, Halogenation, N-(4-bromo-3-methylphenyl)-2-phenylacetamide, N-(4-chloro-3-methylphenyl)-2-phenylacetamide, N-diarylacetamides
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	01 Jul 2019 11:01
Last Modified:	21 Jul 2022 10:17
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3941

Actions (login required)

View Item