The effect of intramolecular interactions on hydrogen bond acidityElectronic supplementary information (ESI) available: summary of retrained regression using DFT methods. See http://www.rsc.org/suppdata/ob/b3/b300598d

Autor:	James Alexis Platts, Farah T.T. Huque
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Range (particle radiation) Base (chemistry) Chemistry Hydrogen bond Intramolecular force Organic Chemistry Intermolecular force Molecule Physical and Theoretical Chemistry Photochemistry Biochemistry
Zdroj:	Organic & Biomolecular Chemistry. 1:1419-1424
ISSN:	1477-0539 1477-0520
DOI:	10.1039/b300598d
Popis:	DFT calculations on a range of molecules containing intramolecular hydrogen bonds are reported, with a view to establishing how intramolecular hydrogen bonding affects their intermolecular interactions. It is shown that properties such as the energy of the intramolecular H-bond are unrelated to the ability to form external H-bonds. Conversely, several properties of complexes with a reference base correlate well with an experimental scale of H-bond acidity, and accurate predictive models are determined. A more detailed study, using electrostatic and overlap properties of complexes with a reference base, is used to predict the location, as well as strength, of hydrogen bond acidity. The effects of intramolecular hydrogen bonding on acidity can be seen not just on O–H and N–H, where acidity is greatly reduced, but also on certain C–H groups, which in some cases become the primary source of acidity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::41682c59eacebfef5f56267ea8bd56da https://doi.org/10.1039/b300598d Zobrazit plný text záznamu