Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid

Charmaine Arderne; Denise K. Olivier; Derek T. Ndinteh

doi:10.1107/S2053229615001047

Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid

Charmaine Arderne, Denise K. Olivier, Derek T. Ndinteh

Chemical Sciences

University of Johannesburg

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The 100K structures of two salts, namely 2-amino-1H-benzimidazolium 3-phenylpropynoate, C₇H₈N₃⁺·C₉H₅O₂^-, (I), and 2-amino-1H-benzimidazolium oct-2-ynoate, C₇H₈N₃⁺·C₈H₁₁O₂^-, (II), both have monoclinic symmetry (space group P21/c) and display N-H⋯O hydrogen bonding. Both structures show packing with corrugated sheets of hydrogen-bonded molecules lying parallel to the [001] direction. Two hydrogen-bonded ring motifs can be identified and described with graph sets R² 2(8) and R⁴ 4(16), respectively, in both (I) and (II). Computational chemistry calculations performed on both compounds show that the hydrogen-bonded ion pairs are more energetically favourable in the crystal structure than their hydrogen-bonded neutral molecule counterparts.

Original language	English
Pages (from-to)	146-151
Number of pages	6
Journal	Acta crystallographica. Section C, Structural chemistry
Volume	71
Issue number	2
DOIs	https://doi.org/10.1107/S2053229615001047
Publication status	Published - 1 Feb 2015

Keywords

amine/acid salts
antimicrobial properties
computational chemistry
crystal structure
DFT analysis
ion pairs
pharmacologically active compounds

ASJC Scopus subject areas

Condensed Matter Physics
Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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title = "Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid",

abstract = "The 100K structures of two salts, namely 2-amino-1H-benzimidazolium 3-phenylpropynoate, C7H8N3+·C9H5O2-, (I), and 2-amino-1H-benzimidazolium oct-2-ynoate, C7H8N3+·C8H11O2-, (II), both have monoclinic symmetry (space group P21/c) and display N-H⋯O hydrogen bonding. Both structures show packing with corrugated sheets of hydrogen-bonded molecules lying parallel to the [001] direction. Two hydrogen-bonded ring motifs can be identified and described with graph sets R2 2(8) and R4 4(16), respectively, in both (I) and (II). Computational chemistry calculations performed on both compounds show that the hydrogen-bonded ion pairs are more energetically favourable in the crystal structure than their hydrogen-bonded neutral molecule counterparts.",

keywords = "amine/acid salts, antimicrobial properties, computational chemistry, crystal structure, DFT analysis, ion pairs, pharmacologically active compounds",

author = "Charmaine Arderne and Olivier, {Denise K.} and Ndinteh, {Derek T.}",

note = "Publisher Copyright: {\textcopyright} 2015 International Union of Crystallography.",

year = "2015",

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doi = "10.1107/S2053229615001047",

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journal = "Acta crystallographica. Section C, Structural chemistry",

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T1 - Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid

AU - Arderne, Charmaine

AU - Olivier, Denise K.

AU - Ndinteh, Derek T.

PY - 2015/2/1

Y1 - 2015/2/1

N2 - The 100K structures of two salts, namely 2-amino-1H-benzimidazolium 3-phenylpropynoate, C7H8N3+·C9H5O2-, (I), and 2-amino-1H-benzimidazolium oct-2-ynoate, C7H8N3+·C8H11O2-, (II), both have monoclinic symmetry (space group P21/c) and display N-H⋯O hydrogen bonding. Both structures show packing with corrugated sheets of hydrogen-bonded molecules lying parallel to the [001] direction. Two hydrogen-bonded ring motifs can be identified and described with graph sets R2 2(8) and R4 4(16), respectively, in both (I) and (II). Computational chemistry calculations performed on both compounds show that the hydrogen-bonded ion pairs are more energetically favourable in the crystal structure than their hydrogen-bonded neutral molecule counterparts.

AB - The 100K structures of two salts, namely 2-amino-1H-benzimidazolium 3-phenylpropynoate, C7H8N3+·C9H5O2-, (I), and 2-amino-1H-benzimidazolium oct-2-ynoate, C7H8N3+·C8H11O2-, (II), both have monoclinic symmetry (space group P21/c) and display N-H⋯O hydrogen bonding. Both structures show packing with corrugated sheets of hydrogen-bonded molecules lying parallel to the [001] direction. Two hydrogen-bonded ring motifs can be identified and described with graph sets R2 2(8) and R4 4(16), respectively, in both (I) and (II). Computational chemistry calculations performed on both compounds show that the hydrogen-bonded ion pairs are more energetically favourable in the crystal structure than their hydrogen-bonded neutral molecule counterparts.

KW - amine/acid salts

KW - antimicrobial properties

KW - computational chemistry

KW - crystal structure

KW - DFT analysis

KW - ion pairs

KW - pharmacologically active compounds

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U2 - 10.1107/S2053229615001047

DO - 10.1107/S2053229615001047

M3 - Article

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AN - SCOPUS:84922523220

SN - 2053-2296

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EP - 151

JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

IS - 2

ER -

Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid

Abstract

Keywords

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