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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dc.contributor.authorLemmerer A.
dc.contributor.authorEsterhuysen C.
dc.date.accessioned2011-10-13T16:59:09Z
dc.date.available2011-10-13T16:59:09Z
dc.date.issued2011
dc.description.abstractThe 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. © The Royal Society of Chemistry 2011.
dc.description.versionArticle
dc.identifier.citationCrystEngComm
dc.identifier.citation13
dc.identifier.citation19
dc.identifier.citationhttp://www.scopus.com/inward/record.url?eid=2-s2.0-80052751080&partnerID=40&md5=ca3ecb5872c070ba189642606d6fddd2
dc.identifier.issn14668033
dc.identifier.other10.1039/c1ce05442b
dc.identifier.urihttp://hdl.handle.net/10019.1/16997
dc.titleOHphenol⋯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
dc.typeArticle
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