Predicting experimental complexation-induced changes in (1)H NMR chemical shift for complexes between zinc-porphyrins and amines using the ab initio/GIAO-HF methodology

Rosa M Gomila; David Quiñonero; Carmen Rotger; Carolina Garau; Antonio Frontera; Pablo Ballester; Antonio Costa; Pere M Deyà

doi:10.1021/ol0170962

Predicting experimental complexation-induced changes in (1)H NMR chemical shift for complexes between zinc-porphyrins and amines using the ab initio/GIAO-HF methodology

Org Lett. 2002 Feb 7;4(3):399-401. doi: 10.1021/ol0170962.

Authors

Rosa M Gomila¹, David Quiñonero, Carmen Rotger, Carolina Garau, Antonio Frontera, Pablo Ballester, Antonio Costa, Pere M Deyà

Affiliation

¹ Department of Chemistry, Universitat de les Illes Balears, 07071 Palma de Mallorca, Spain.

PMID: 11820889
DOI: 10.1021/ol0170962

Abstract

Ab initio calculations were carried out on zinc-porphyrins complexed to several amines: N-(3,5-dimethyl-pyridin-4-yl)-formamide, 1,4-diazabiciclo[2.2.2]octane (DABCO), and 1-azabiciclo[2.2.2]octane (quinuclidine). The proton chemical shifts of these complexes were calculated ab initio at the GIAO-HF/6-311G//HF/3-21G level of theory, and the obtained values agree satisfactorily with experimental results. The complexation-induced changes in (1)H NMR chemical shifts correlate well with differences in association constants of several host-guest complexes.