Issue 19, 2011
From the journal:

CrystEngComm

OHphenol⋯OHalcohol hydrogen-bonding as the preferred hydrogen-bonded interaction in the crystal structures of three isomers of methylolphenol: analysis of hydrogen-bonding interactions in phenol and alcohol containing molecules†‡

Andreas Lemmerer*a  and  Catharine Esterhuysenb  

* Corresponding authors

a Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, South Africa
E-mail: andreas.lemmerer@wits.ac.za
Fax: +27 11 7176 749
Tel: +27 11 717 6711

b Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa
E-mail: ce@sun.ac.za
Fax: +27 21 808 3360
Tel: +27 21 808 3345

Abstract

The crystal structures of three isomers containing a phenol and an alcohol functional group, 2-methylolphenol (1), 3-methylolphenol (2) and 4-methylolphenol (3) are reported. All isomers feature heteromeric hydrogen bonded interactions, either from the phenol hydrogen to the alcohol O or from the alcohol hydrogen to the phenol O. There are no homomeric interactions present in the solid state. An analysis of 31 related compounds shows that in the literature the OHphenol⋯OHalcohol hydrogen bond is the most commonly seen heteromeric interaction in these types of compounds, and DFT calculations show that this hydrogen bond has the highest interaction energy in the three isomers. The isomer 3-methylolphenol (2) crystallizes as two concomitant polymorphs, 2a containing two molecules in the asymmetric unit, and 2b containing three molecules in the asymmetric unit, with the former slightly more stable according to DFT calculations.

Graphical abstract: OHphenol⋯OHalcohol hydrogen-bonding as the preferred hydrogen-bonded interaction in the crystal structures of three isomers of methylolphenol: analysis of hydrogen-bonding interactions in phenol and alcohol containing molecules

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Article information

DOI
https://doi.org/10.1039/C1CE05442B
Article type
Paper
Submitted
13 Apr 2011
Accepted
14 Jun 2011
First published
25 Jul 2011

CrystEngComm, 2011,13, 5773-5782

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OHphenol⋯OHalcohol hydrogen-bonding as the preferred hydrogen-bonded interaction in the crystal structures of three isomers of methylolphenol: analysis of hydrogen-bonding interactions in phenol and alcohol containing molecules

A. Lemmerer and C. Esterhuysen, CrystEngComm, 2011, 13, 5773 DOI: 10.1039/C1CE05442B

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