2-(2-Acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid and 2-(2-acetylamino-5-methylphenyl)-2,2-difluoroethanoic acid, and 2-(2-acetylaminophenyl)-2,2-difluoro-N-phenylacetamide and 2-(2-acetylaminophenyl)-N-(4-chlorophenyl)-2,2-difluoroacetamide: examples of variation in molecular packing and hydrogen-bonding motif induced by substituent change

N Boechat, L C Maciel, A C Pinto, S M S V Wardell, J M S Skakle, R A Howie

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Abstract

Among the title compounds, viz. the acids C10H8ClF2NO3, (I), and C11H11F2NO3, (II), and the amides C14H14F2N2O2, (III), and C14H13ClF2N2O2, (IV), the change of substituent from Cl in (I) to methyl in (II) has a dramatic effect upon the hydrogen bonding between the molecules, which occur in layers in both cases. In the structures of (III) and (IV), hydrogen bonds connect the molecules to form chains, but the introduction of a chloro substituent in (IV) has a profound effect on the orientation of the molecules within the chains and the packing of the chains in the structure as a whole.

Original languageEnglish
Pages (from-to)o270-o275
Number of pages6
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume61
Issue number5
DOIs
Publication statusPublished - May 2005

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Hydrogen Bonding
Amides
Hydrogen
Hydrogen bonds
Molecules
Acids
acetanilide
2-(2-acetylaminophenyl)-N-(4-chlorophenyl)-2,2-difluoroacetamide
2-(2-acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid

Cite this

@article{4555cedfd3694766a46d4405ba8318ef,
title = "2-(2-Acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid and 2-(2-acetylamino-5-methylphenyl)-2,2-difluoroethanoic acid, and 2-(2-acetylaminophenyl)-2,2-difluoro-N-phenylacetamide and 2-(2-acetylaminophenyl)-N-(4-chlorophenyl)-2,2-difluoroacetamide: examples of variation in molecular packing and hydrogen-bonding motif induced by substituent change",
abstract = "Among the title compounds, viz. the acids C10H8ClF2NO3, (I), and C11H11F2NO3, (II), and the amides C14H14F2N2O2, (III), and C14H13ClF2N2O2, (IV), the change of substituent from Cl in (I) to methyl in (II) has a dramatic effect upon the hydrogen bonding between the molecules, which occur in layers in both cases. In the structures of (III) and (IV), hydrogen bonds connect the molecules to form chains, but the introduction of a chloro substituent in (IV) has a profound effect on the orientation of the molecules within the chains and the packing of the chains in the structure as a whole.",
author = "N Boechat and Maciel, {L C} and Pinto, {A C} and Wardell, {S M S V} and Skakle, {J M S} and Howie, {R A}",
year = "2005",
month = "5",
doi = "10.1107/S0108270105007547",
language = "English",
volume = "61",
pages = "o270--o275",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",
number = "5",

}

TY - JOUR

T1 - 2-(2-Acetylamino-5-chlorophenyl)-2,2-difluoroethanoic acid and 2-(2-acetylamino-5-methylphenyl)-2,2-difluoroethanoic acid, and 2-(2-acetylaminophenyl)-2,2-difluoro-N-phenylacetamide and 2-(2-acetylaminophenyl)-N-(4-chlorophenyl)-2,2-difluoroacetamide: examples of variation in molecular packing and hydrogen-bonding motif induced by substituent change

AU - Boechat, N

AU - Maciel, L C

AU - Pinto, A C

AU - Wardell, S M S V

AU - Skakle, J M S

AU - Howie, R A

PY - 2005/5

Y1 - 2005/5

N2 - Among the title compounds, viz. the acids C10H8ClF2NO3, (I), and C11H11F2NO3, (II), and the amides C14H14F2N2O2, (III), and C14H13ClF2N2O2, (IV), the change of substituent from Cl in (I) to methyl in (II) has a dramatic effect upon the hydrogen bonding between the molecules, which occur in layers in both cases. In the structures of (III) and (IV), hydrogen bonds connect the molecules to form chains, but the introduction of a chloro substituent in (IV) has a profound effect on the orientation of the molecules within the chains and the packing of the chains in the structure as a whole.

AB - Among the title compounds, viz. the acids C10H8ClF2NO3, (I), and C11H11F2NO3, (II), and the amides C14H14F2N2O2, (III), and C14H13ClF2N2O2, (IV), the change of substituent from Cl in (I) to methyl in (II) has a dramatic effect upon the hydrogen bonding between the molecules, which occur in layers in both cases. In the structures of (III) and (IV), hydrogen bonds connect the molecules to form chains, but the introduction of a chloro substituent in (IV) has a profound effect on the orientation of the molecules within the chains and the packing of the chains in the structure as a whole.

U2 - 10.1107/S0108270105007547

DO - 10.1107/S0108270105007547

M3 - Article

VL - 61

SP - o270-o275

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

IS - 5

ER -