Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivative

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C-H⋯O intermolecular hydrogen bonds. In most cases the C atom of the C-H unit was a member of the aromatic ring. Intramolecular (olefinic) C-H⋯O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C-C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C-H⋯O hydrogen bonding. Here, the C atom of the C-H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The β-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.

Original languageEnglish
Pages (from-to)216-220
Number of pages5
JournalActa Crystallographica Section B
Volume55
Issue number2
Publication statusPublished - Apr 1 1999

Fingerprint

Hydrogen Bonding
Phase structure
esters
Hydrogen bonds
Esters
Crystalline materials
Derivatives
acids
hydrogen
Atoms
interactions
Conformations
Hydrogen
hydrogen bonds
atoms
Acids
rings
workstations
carboxyl group
Dimers

ASJC Scopus subject areas

  • Structural Biology
  • Condensed Matter Physics

Cite this

Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivative. / Pálinkó, I.

In: Acta Crystallographica Section B, Vol. 55, No. 2, 01.04.1999, p. 216-220.

Research output: Contribution to journalArticle

@article{cfb1cd2d2cf74dcc964f0d2ccdb329c2,
title = "Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivative",
abstract = "Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C-H⋯O intermolecular hydrogen bonds. In most cases the C atom of the C-H unit was a member of the aromatic ring. Intramolecular (olefinic) C-H⋯O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C-C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C-H⋯O hydrogen bonding. Here, the C atom of the C-H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The β-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.",
author = "I. P{\'a}link{\'o}",
year = "1999",
month = "4",
day = "1",
language = "English",
volume = "55",
pages = "216--220",
journal = "Acta Crystallographica Section B: Structural Science",
issn = "0108-7681",
publisher = "International Union of Crystallography",
number = "2",

}

TY - JOUR

T1 - Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivative

AU - Pálinkó, I.

PY - 1999/4/1

Y1 - 1999/4/1

N2 - Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C-H⋯O intermolecular hydrogen bonds. In most cases the C atom of the C-H unit was a member of the aromatic ring. Intramolecular (olefinic) C-H⋯O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C-C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C-H⋯O hydrogen bonding. Here, the C atom of the C-H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The β-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.

AB - Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C-H⋯O intermolecular hydrogen bonds. In most cases the C atom of the C-H unit was a member of the aromatic ring. Intramolecular (olefinic) C-H⋯O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C-C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C-H⋯O hydrogen bonding. Here, the C atom of the C-H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The β-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.

UR - http://www.scopus.com/inward/record.url?scp=0343940639&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343940639&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0343940639

VL - 55

SP - 216

EP - 220

JO - Acta Crystallographica Section B: Structural Science

JF - Acta Crystallographica Section B: Structural Science

SN - 0108-7681

IS - 2

ER -