How H-bonding affects aromaticity of the ring in variously substituted phenol complexes with bases. 4. Molecular geometry as a source of chemical information

Tadeusz M Krygowski; Halina Szatyłowicz; Joanna E Zachara

doi:10.1021/ci049817s

How H-bonding affects aromaticity of the ring in variously substituted phenol complexes with bases. 4. Molecular geometry as a source of chemical information

J Chem Inf Comput Sci. 2004 Nov-Dec;44(6):2077-82. doi: 10.1021/ci049817s.

Authors

Tadeusz M Krygowski¹, Halina Szatyłowicz, Joanna E Zachara

Affiliation

¹ Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland.

PMID: 15554678
DOI: 10.1021/ci049817s

Abstract

Aromaticity of the ring of variously substituted phenols in their H-bonded complexes with various bases was a subject of analysis based on 664 geometries retrieved from CSD and by use of the aromaticity index HOMA. GEO and EN, the components of the HOMA index, describing a decrease of aromaticity due to an increase of bond alternation (GEO term) and bond elongation (EN term), were also studied. There is an approximate monotonic dependence of HOMA and GEO on the H-bond strength estimated by the C-O bond length of the hydroxyl group in phenols.