Structural characteristics of intramolecular hydrogen bonding in benzene derivatives

Attila Kovács, Andrea Szabó, I. Hargittai

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

In this Account, the intramolecular hydrogen bonding (HB) properties of various proton acceptor groups (BXn: C=N, NO2, C= O, P=O, F, CF3) with OH and NH2 (AH) in benzene derivatives are assessed on the basis of gas electron diffraction, spectroscopic, and quantum chemical results. The most important properties are the HB energy, the characteristic geometrical changes in the interacting groups (lengthening of the A-H and B-X, shortening of the C-A and C-B bonds) and in the benzene ring, and the vibrational properties of the AH groups. These properties are characteristic of the particular HB interaction (in particular of the AH and BXn pair in single and multiple hydrogen-bonded systems); however, they cannot be related directly to the computed HB energies.

Original languageEnglish
Pages (from-to)887-894
Number of pages8
JournalAccounts of Chemical Research
Volume35
Issue number10
DOIs
Publication statusPublished - Oct 2002

Fingerprint

Benzene Derivatives
Hydrogen bonds
Benzene
Electron diffraction
Protons
Hydrogen

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Structural characteristics of intramolecular hydrogen bonding in benzene derivatives. / Kovács, Attila; Szabó, Andrea; Hargittai, I.

In: Accounts of Chemical Research, Vol. 35, No. 10, 10.2002, p. 887-894.

Research output: Contribution to journalArticle

@article{8dee1a28e81d4c6484c376b11afe423d,
title = "Structural characteristics of intramolecular hydrogen bonding in benzene derivatives",
abstract = "In this Account, the intramolecular hydrogen bonding (HB) properties of various proton acceptor groups (BXn: C=N, NO2, C= O, P=O, F, CF3) with OH and NH2 (AH) in benzene derivatives are assessed on the basis of gas electron diffraction, spectroscopic, and quantum chemical results. The most important properties are the HB energy, the characteristic geometrical changes in the interacting groups (lengthening of the A-H and B-X, shortening of the C-A and C-B bonds) and in the benzene ring, and the vibrational properties of the AH groups. These properties are characteristic of the particular HB interaction (in particular of the AH and BXn pair in single and multiple hydrogen-bonded systems); however, they cannot be related directly to the computed HB energies.",
author = "Attila Kov{\'a}cs and Andrea Szab{\'o} and I. Hargittai",
year = "2002",
month = "10",
doi = "10.1021/ar020003b",
language = "English",
volume = "35",
pages = "887--894",
journal = "Accounts of Chemical Research",
issn = "0001-4842",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Structural characteristics of intramolecular hydrogen bonding in benzene derivatives

AU - Kovács, Attila

AU - Szabó, Andrea

AU - Hargittai, I.

PY - 2002/10

Y1 - 2002/10

N2 - In this Account, the intramolecular hydrogen bonding (HB) properties of various proton acceptor groups (BXn: C=N, NO2, C= O, P=O, F, CF3) with OH and NH2 (AH) in benzene derivatives are assessed on the basis of gas electron diffraction, spectroscopic, and quantum chemical results. The most important properties are the HB energy, the characteristic geometrical changes in the interacting groups (lengthening of the A-H and B-X, shortening of the C-A and C-B bonds) and in the benzene ring, and the vibrational properties of the AH groups. These properties are characteristic of the particular HB interaction (in particular of the AH and BXn pair in single and multiple hydrogen-bonded systems); however, they cannot be related directly to the computed HB energies.

AB - In this Account, the intramolecular hydrogen bonding (HB) properties of various proton acceptor groups (BXn: C=N, NO2, C= O, P=O, F, CF3) with OH and NH2 (AH) in benzene derivatives are assessed on the basis of gas electron diffraction, spectroscopic, and quantum chemical results. The most important properties are the HB energy, the characteristic geometrical changes in the interacting groups (lengthening of the A-H and B-X, shortening of the C-A and C-B bonds) and in the benzene ring, and the vibrational properties of the AH groups. These properties are characteristic of the particular HB interaction (in particular of the AH and BXn pair in single and multiple hydrogen-bonded systems); however, they cannot be related directly to the computed HB energies.

UR - http://www.scopus.com/inward/record.url?scp=0036798197&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036798197&partnerID=8YFLogxK

U2 - 10.1021/ar020003b

DO - 10.1021/ar020003b

M3 - Article

C2 - 12379141

AN - SCOPUS:0036798197

VL - 35

SP - 887

EP - 894

JO - Accounts of Chemical Research

JF - Accounts of Chemical Research

SN - 0001-4842

IS - 10

ER -