𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Intramolecular hydrogen bond energy and cooperative interactions in α-, β-, and γ-cyclodextrin conformers

✍ Scribed by Milind M. Deshmukh; Libero J. Bartolotti; Shridhar R. Gadre

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
297 KB
Volume
32
Category
Article
ISSN
0192-8651

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Accurate estimation of individual intramolecular hydrogen bond (H‐bond) energies is an intricate task for multiply H‐bonded systems. In such cases, the hydrogen bond strengths could be highly influenced by the cooperative interactions, for example, those between hydroxyl groups in sugars. In this work, we use the recently proposed molecular tailoring approach‐based quantification (Deshmukh, Gadre, and Bartolotti, J Phys Chem A 2006, 110, 12519) to the extended systems of cyclodextrins (CDs). Further, the structure and stability of different conformers of α‐, β‐, and γ‐CDs are explained based on the energetics and cooperative contribution to the strength of these H‐bonds. The estimated OH···O H‐bond energies in the various CD conformers are found to vary widely from 1.1 to 8.3 kcal mol^−1^. The calculated energy contributions to cooperativity toward the H‐bond strengths fall in the range of 0.25–2.75 kcal mol^−1^. © 2011 Wiley Periodicals, Inc. J Comput Chem, 2011

📜 SIMILAR VOLUMES

Intramolecular interactions and intramol
Intramolecular interactions and intramolecular hydrogen bonding in conformers of gaseous glycine
✍ L. F. Pacios; P. C. Gómez 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 248 KB

## Abstract __Ab initio__ calculations at the MP2/6‐311++G\*\* level of theory led recently to the identification of 13 stable conformers of gaseous glycine with relative energies within 11 kcal/mol. The stability of every structure depends on subtle intramolecular effects arising from conformation

Conformational study of a guaiacyl β-O-4
Conformational study of a guaiacyl β-O-4 lignin model compound by NMR. Examination of intramolecular hydrogen bonding interactions and conformational flexibility in solution
✍ Stéphane Besombes; Jean-Pierre Utille; Karim Mazeau; Danielle Robert; François R 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 English ⚖ 258 KB

## Abstract Intramolecular H‐bonding interactions were investigated in solution for the __threo__ and __erythro__ diastereomeric forms of a guaiacyl β‐O‐4 lignin model compound by using the NMR data obtained from hydroxyl protons. Temperature coefficients of the chemical shifts (dδ/d__T__) and coup

Conformations, energies, and intramolecu
Conformations, energies, and intramolecular hydrogen bonds in dicarboxylic acids: Implications for the design of synthetic dicarboxylic acid receptors
✍ Thanh Ha Nguyen; David E. Hibbs; Siân T. Howard 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 191 KB

## Abstract The various conformers of the dicarboxylic acids HO~2~C(CH2)~__n__~CO~2~H, __n__ = 1–4, were obtained using density functional methods (DFT), both in the gas phase and in the aqueous phase using a polarized continuum model (PCM). Several new conformers were identified, particularly fo