How strong is a π-facial hydrogen bond?
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 22,p. 2531-2532
- https://doi.org/10.1039/cc9960002531
Abstract
Functional group substitutions (chemical mutations) in a molecular zipper complex have been used to construct a thermodynamic cycle for estimating the strength of a π-facial H-bond between an NH group and an aromatic ring resulting in a lower limit of –4.5 ± 0.5 kJ mol–1 for the magnitude of the intermolecular NH-π interaction in chloroform.Keywords
This publication has 11 references indexed in Scilit:
- Chemical Double‐Mutant Cycles for the Measurement of Weak Intermolecular Interactions: Edge‐to‐Face Aromatic InteractionsAngewandte Chemie International Edition in English, 1996
- Application of a generalised enthalpy–entropy relationship to binding co-operativity and weak associations in solutionJournal of the Chemical Society, Perkin Transactions 2, 1995
- Decomposition of the Free Energy of a System in Terms of Specific InteractionsJournal of Molecular Biology, 1994
- Meldola Lecture. The role of aromatic interactions in molecular recognitionChemical Society Reviews, 1994
- Amino/aromatic interactionsNature, 1993
- Hydrogen bonding in the benzene–ammonia dimerNature, 1993
- Amino–aromatic interaction between histidine 197 of the neurokinin-1 receptor and CP 96345Nature, 1993
- Structural consequences of a molecular assembly that is deficient in hydrogen-bond acceptorsJournal of the Chemical Society, Chemical Communications, 1992
- Molecular recognition. 2. Molecular recognition of amino acids: two-point fixation of amino acids with bifunctional metalloporphyrin receptorsJournal of the American Chemical Society, 1988
- Aromatic rings act as hydrogen bond acceptorsJournal of Molecular Biology, 1988