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Carver FJ, Hunter CA, Jones PS, et al. Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles. Chemistry. 2001;7(22):4854-62doi: 10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#.
Carver, F. J., Hunter, C. A., Jones, P. S., Livingstone, D. J., McCabe, J. F., Seward, E. M., Tiger, P., & Spey, S. E. (2001). Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles. Chemistry (Weinheim an der Bergstrasse, Germany), 7(22), 4854-62. https://doi.org/10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#
Carver, F J, et al. "Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 7,22 (2001): 4854-62. doi: https://doi.org/10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#
Carver FJ, Hunter CA, Jones PS, Livingstone DJ, McCabe JF, Seward EM, Tiger P, Spey SE. Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles. Chemistry. 2001 Nov 19;7(22):4854-62. doi: 10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#. PMID: 11763454.
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Chemistry. 2001 Nov 19;7(22):4854-62. doi: 10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#.

Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles.

Chemistry (Weinheim an der Bergstrasse, Germany)

F J Carver, C A Hunter, P S Jones, D J Livingstone, J F McCabe, E M Seward, P Tiger, S E Spey

Affiliations

  1. Centre for Chemical Biology, Krebs Institute for Biomolecular Science, Department of Chemistry, University of Sheffield, UK.

PMID: 11763454 DOI: 10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#

Abstract

Synthetic H-bonded zipper complexes have been used to quantify the magnitude of an edge-to-face aromatic interaction between a benzoyl group and an aniline ring. Four chemical double-mutant cycles were constructed by using a matrix of nine closely related complexes in which the aromatic rings were sequentially substituted for alkyl substituents. The stability constants and three-dimensional structures of the complexes were determined by using 1H NMR titrations in deuterochloroform at room temperature. The value of the interaction energy is similar in all cases, the average is -1.4 +/- 0.5 kJ mol(-1). The scope and limitations of the double-mutant approach are explored, and the consequences of conformational equilibria are discussed.

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