Enthalpy (ΔH) and entropy (ΔS) for π-stacking interactions in near-sandwich configurations: Relative importance of electrostatic, dispersive, and charge-transfer effects

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2469-2475

  Gung, Benjamin W ^a   Xue, Xiaowen ^a   Zou, Yan ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHARGE TRANSFER; CONFORMATIONS; ENTHALPY; ENTROPY; GROUND STATE; MOLECULAR MODELING;

ARENES; MOLECULAR MODELS; REPULSIVE INTERACTIONS; TRIPTYCENE;

MOLECULAR INTERACTIONS;

AROMATIC COMPOUND; BENZOIC ACID DERIVATIVE; FLUORINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIPTYCENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; ENTHALPY; ENTROPY; ISOMER; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; STEREOSPECIFICITY; ELECTRICITY; ELECTRON; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE; THERMODYNAMICS;

ELECTRONS; ELECTROSTATICS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TEMPERATURE; THERMODYNAMICS;

EID: 34047202392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062526t     Document Type: Article

References (29)

1. Kool, E. T.; Morales, J. C.; Guckian, K. M. Mimicking the structure and function of DNA: Insights into DNA stability and replication. Angew. Chem., Int. Ed. 2000, 39, 990-1009.
2. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Phenyl-perfluorophenyl stacking interactions: a new strategy for supermolecule construction. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
3. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. Aromatic interactions. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
4. Waters, M. L. Aromatic interactions in model systems. Curr. Opin. Chem. Biol. 2002, 6, 736-741.
5. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with aromatic rings in chemical and biological recognition. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
6. Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. Polar/π Interactions between Stacked Aryls in 1,8-Diarylnaphthalenes. J. Am. Chem. Soc. 1992, 114, 5729-5733.
7. Cozzi, F.; Cinquini, M.; Annuziata, R.; Siegel, J. S. Dominance of Polar/π over Charge-Transfer Effects in Stacked Phenyl Interactions. J. Am. Chem. Soc. 1993, 115, 5330-5331.
8. Adams, H.; Blanco, J. L.; Chessari, G.; Hunter, C. A.; Low, C. M.; Sanderson, J. M.; Vinter, J. G. Quantitative determination of intermolecular interactions with fluorinated aromatic rings. Chem.-Eur. J. 2001, 7, 3494-3503.
9. Cockroft, S. L.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. Electrostatic Control of Aromatic Stacking Interactions. J. Am. Chem. Soc. 2005, 127, 8594-8595.
10. Schneider, H. J. Requirements for quantifications of weak intermolecular interactions from equilibrium studies with supramolecular complexes. Angew. Chem., Int. Ed. Engl. 1997, 36, 1072-1073.
11. Martinez, A. G.; Barcina, J. O.; Cerezo, A. D. Influence of highly preorganised 7,7-diphenylnorbornane in the free energy of edge-to-face aromatic interactions. Chem.-Eur. J. 2001, 7, 1171-1175.
12. Paliwal, S.; Geib, S.; Wilcox, C. S. Chemistry of Synthetic Receptors and Functional-Group Arrays. 24. Molecular Torsion Balance for Weak Molecular Recognition Forces-Effects of Tilted-T Edge-to-Face Aromatic Interactions on Conformational Selection and Solid-State Structure. J. Am. Chem. Soc. 1994, 116, 4497-4498.
13. Kim, E.; Paliwal, S.; Wilcox, C. S. Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition. J. Am. Chem. Soc. 1998, 120, 11192-11193.
14. Jennings, W. B.; Farrell, B. M.; Malone, J. F. Attractive intramolecular edge-to-face aromatic interactions in flexible organic molecules. Acc. Chem. Res. 2001, 34, 885-894.
15. Gung, B. W.; Xue, X. W.; Reich, H. J. The strength of parallel-displaced arene-arene interactions in chloroform. J. Org. Chem. 2005, 70, 3641-3644.
16. Gung, B. W.; Patel, M.; Xue, X. W. A threshold for charge transfer in aromatic interactions? A quantitative study of π-stacking interactions. J. Org. Chem. 2005, 70, 10532-10537.
17. Williams, J. H. The Molecular Electric Quadrupole-Moment and Solid-State Architecture. Acc. Chem. Res. 1993, 26, 593-598.
18. Luhmer, M.; Bartik, K.; Dejaegere, A.; Bovy, P.; Reisse, J. The Importance Of Quadrupolar Interactions In Molecular Recognition Processes Involving A Phenyl Group. Bull. Soc. Chim. Fr. 1994, 131, 603-606.
19. Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Polar interactions between stacked p systems in fluorinated 1,8-diarylnaphthalenes: importance of quadrupole moments in molecular recognition. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019-1020.
20. Ma, J. C.; Dougherty, D. A. The cation-π interaction. Chem. Rev. 1997, 97, 1303-1324.
21. 5X Stacking Interactions. J. Org. Chem. 2006, 71, 9261-9270.
22. Sinnokrot, M. O.; Sherrill, C. D. Substituent effects in π-π interactions: Sandwich and T-shaped configurations. J. Am. Chem. Soc. 2004, 126, 7690-7697.
23. 3-O hydrogen bond. Implications of its presence from the substituent effects on the populations of rotamers in 4-substituted 9-ethyl-1-methoxytriptycenes and 9-(substituted | phenoxymethyl)-1,4-dimethyltriptycenes. Bull. Chem. Soc. Jpn. 1987, 60, 1781-1788.
24. Kimura, N. The Role of the Leaving Group in the Dissociation of Radical Anions of 9-(Aryloxymethyl)anthracenes. J. Am. Chem. Soc. 2001, 123, 3824-3825.
25. Glaser, R. Aspirin. An ab Initio Quantum-Mechanical Study of Conformational Preferences and of Neighboring Group Interactions. J. Org. Chem. 2001, 66, 771-779.
26. Gung, B. W.; Xue, X. W.; Reich, H. J. Off-center oxygen-arene interactions in solution: A quantitative study. J. Org. Chem. 2005, 70, 7232-7237.
27. Shoemaker, D. P.; Garland, C. W.; Nibler, J. W. Experiments in Physical Chemistry, 6th ed.; McGraw-Hill: New York, 1996.
28. Leffler, J. E.; Granwald, E. Rates and equilibria of organic reactions as treated by statistical, thermodynamic, and extrathermodynamic methods; Wiley: New York, 1963.
29. Tsuzuki, S.; Uchimaru, T.; Mikami, M. Intermolecular interaction between hexafluorobenzene and benzene: Ab initio calculations including CCSD(T) level electron correlation correction. J. Phys. Chem. A 2006, 110, 2027-2033.