Intra- and intermolecular hydrogen bonding in 2-phosphinylphenol: A quantum chemical study

Jack B. Levy, Ned H. Martin, I. Hargittai, M. Hargittai

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A computational study of 2-phosphinylphenol has been carried out to investigate intramolecular hydrogen bond formation and its consequences in the rest of the molecule. This is an extension of both our synthetic work on organophosphorus derivatives of diphenyl ether and our experimental and computational structure analyses of salicylaldehyde, 2-nitrophenol, and related molecules. Full optimization of the 2-phosphinylphenol geometries was carried out both at the HF/6-31+G** level and, to include electron correlation, at the MP2/ 6-31G* level. The stabilization energy of the intramolecular hydrogen bonding in 2-phosphinylphenol (28.4 kJ/mol by isodesmic calculation) is smaller than that of the intermolecular hydrogen bonding in the dimer of 2-phosphinylphenol, also computed in this work to be 59.1 kJ/mol per hydrogen bond from the counterpoise interaction energy or 57.4 kJ/mol by BSSE-corrected isodesmic calculation. The closure of the six-membered ring with the intramolecular hydrogen bond apparently introduces energy-costing constraints. The geometrical changes in 2-phosphinylphenol accompanying the formation of the hydrogen bond are similar to those observed in 2-nitrophenol and salicylaldehyde, characterized as resonance-assisted hydrogen bonding. In addition to the lowest energy monomer with the hydrogen bond, two further stable minima of higher energy with no hydrogen bonding were found for 2-phosphinylphenol.

Original languageEnglish
Pages (from-to)274-279
Number of pages6
JournalJournal of Physical Chemistry A
Volume102
Issue number1
Publication statusPublished - Jan 1 1998

Fingerprint

Hydrogen bonds
hydrogen bonds
hydrogen
energy
closures
molecules
ethers
monomers
stabilization
dimers
Electron correlations
Molecules
optimization
rings
Dimers
geometry
Stabilization
Monomers
electrons
Derivatives

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Intra- and intermolecular hydrogen bonding in 2-phosphinylphenol : A quantum chemical study. / Levy, Jack B.; Martin, Ned H.; Hargittai, I.; Hargittai, M.

In: Journal of Physical Chemistry A, Vol. 102, No. 1, 01.01.1998, p. 274-279.

Research output: Contribution to journalArticle

@article{30bb2ceb014b4d81bc3f328e40178307,
title = "Intra- and intermolecular hydrogen bonding in 2-phosphinylphenol: A quantum chemical study",
abstract = "A computational study of 2-phosphinylphenol has been carried out to investigate intramolecular hydrogen bond formation and its consequences in the rest of the molecule. This is an extension of both our synthetic work on organophosphorus derivatives of diphenyl ether and our experimental and computational structure analyses of salicylaldehyde, 2-nitrophenol, and related molecules. Full optimization of the 2-phosphinylphenol geometries was carried out both at the HF/6-31+G** level and, to include electron correlation, at the MP2/ 6-31G* level. The stabilization energy of the intramolecular hydrogen bonding in 2-phosphinylphenol (28.4 kJ/mol by isodesmic calculation) is smaller than that of the intermolecular hydrogen bonding in the dimer of 2-phosphinylphenol, also computed in this work to be 59.1 kJ/mol per hydrogen bond from the counterpoise interaction energy or 57.4 kJ/mol by BSSE-corrected isodesmic calculation. The closure of the six-membered ring with the intramolecular hydrogen bond apparently introduces energy-costing constraints. The geometrical changes in 2-phosphinylphenol accompanying the formation of the hydrogen bond are similar to those observed in 2-nitrophenol and salicylaldehyde, characterized as resonance-assisted hydrogen bonding. In addition to the lowest energy monomer with the hydrogen bond, two further stable minima of higher energy with no hydrogen bonding were found for 2-phosphinylphenol.",
author = "Levy, {Jack B.} and Martin, {Ned H.} and I. Hargittai and M. Hargittai",
year = "1998",
month = "1",
day = "1",
language = "English",
volume = "102",
pages = "274--279",
journal = "Journal of Physical Chemistry A",
issn = "1089-5639",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Intra- and intermolecular hydrogen bonding in 2-phosphinylphenol

T2 - A quantum chemical study

AU - Levy, Jack B.

AU - Martin, Ned H.

AU - Hargittai, I.

AU - Hargittai, M.

PY - 1998/1/1

Y1 - 1998/1/1

N2 - A computational study of 2-phosphinylphenol has been carried out to investigate intramolecular hydrogen bond formation and its consequences in the rest of the molecule. This is an extension of both our synthetic work on organophosphorus derivatives of diphenyl ether and our experimental and computational structure analyses of salicylaldehyde, 2-nitrophenol, and related molecules. Full optimization of the 2-phosphinylphenol geometries was carried out both at the HF/6-31+G** level and, to include electron correlation, at the MP2/ 6-31G* level. The stabilization energy of the intramolecular hydrogen bonding in 2-phosphinylphenol (28.4 kJ/mol by isodesmic calculation) is smaller than that of the intermolecular hydrogen bonding in the dimer of 2-phosphinylphenol, also computed in this work to be 59.1 kJ/mol per hydrogen bond from the counterpoise interaction energy or 57.4 kJ/mol by BSSE-corrected isodesmic calculation. The closure of the six-membered ring with the intramolecular hydrogen bond apparently introduces energy-costing constraints. The geometrical changes in 2-phosphinylphenol accompanying the formation of the hydrogen bond are similar to those observed in 2-nitrophenol and salicylaldehyde, characterized as resonance-assisted hydrogen bonding. In addition to the lowest energy monomer with the hydrogen bond, two further stable minima of higher energy with no hydrogen bonding were found for 2-phosphinylphenol.

AB - A computational study of 2-phosphinylphenol has been carried out to investigate intramolecular hydrogen bond formation and its consequences in the rest of the molecule. This is an extension of both our synthetic work on organophosphorus derivatives of diphenyl ether and our experimental and computational structure analyses of salicylaldehyde, 2-nitrophenol, and related molecules. Full optimization of the 2-phosphinylphenol geometries was carried out both at the HF/6-31+G** level and, to include electron correlation, at the MP2/ 6-31G* level. The stabilization energy of the intramolecular hydrogen bonding in 2-phosphinylphenol (28.4 kJ/mol by isodesmic calculation) is smaller than that of the intermolecular hydrogen bonding in the dimer of 2-phosphinylphenol, also computed in this work to be 59.1 kJ/mol per hydrogen bond from the counterpoise interaction energy or 57.4 kJ/mol by BSSE-corrected isodesmic calculation. The closure of the six-membered ring with the intramolecular hydrogen bond apparently introduces energy-costing constraints. The geometrical changes in 2-phosphinylphenol accompanying the formation of the hydrogen bond are similar to those observed in 2-nitrophenol and salicylaldehyde, characterized as resonance-assisted hydrogen bonding. In addition to the lowest energy monomer with the hydrogen bond, two further stable minima of higher energy with no hydrogen bonding were found for 2-phosphinylphenol.

UR - http://www.scopus.com/inward/record.url?scp=0031646385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031646385&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0031646385

VL - 102

SP - 274

EP - 279

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

SN - 1089-5639

IS - 1

ER -