Reciprocal Hydrogen Bonding–Aromaticity Relationships

Autor:	Judy I. Wu, James E. Jackson, Paul von Ragué Schleyer
Rok vydání:	2014
Předmět:	Hydrogen bond Chemistry Stereochemistry Chemical shift Intermolecular force Aromaticity General Chemistry Biochemistry Tautomer Catalysis Delocalized electron Colloid and Surface Chemistry Computational chemistry Reciprocal
Zdroj:	Journal of the American Chemical Society. 136:13526-13529
ISSN:	1520-5126 0002-7863
Popis:	Computed association energies and dissected nucleus-independent chemical shifts (NICS) document the mutual enhancement (or reduction) of intermolecular interactions and the aromaticity of H-bonded substrates. H-bonding interactions that increase cyclic 4n + 2 π-electron delocalization boost aromaticity. Conversely, such interactions are weakened when aromaticity is decreased as a result of more localized quinoidal π character. Representative examples of the tautomeric equilibria of π-conjugated heterocyclic compounds in protic solvents and other H-bonding environments also illustrate such H-bonding/aromaticity interplay.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b4ff10673daac2caaa4339ac19b537ad https://doi.org/10.1021/ja507202f Zobrazit plný text záznamu