Molecular geometry as a source of chemical information. Part 2 - An attempt to estimate the H-bond strength: The case of p-nitrophenol complexes with bases

Journal of Physical Organic Chemistry

Volumn 18, Issue 2, 2005, Pages 110-114

  Krygowski, Tadeusz Marek ^a   Zachara, Joanna Ewa ^a   Szatylowicz, Halina ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Ab initio; H bond; H bond strength; p nitrophenol

Indexed keywords

ALKALINITY; ELECTRONS; GEOMETRY; HYDROGEN BONDS; MOLECULAR STRUCTURE; PHENOLS;

AB INITIO; H-BOND; H-BOND STRENGTH; P-NITROPHENOL;

COMPLEXATION;

EID: 12444273683     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.875     Document Type: Conference Paper

References (43)

1. Jeffrey GA, Saenger W. Hydrogen Bonding in Biological Structures. Springer: Berlin, 1991.
2. Jeffrey GA. An Introduction to Hydrogen Bonding. Oxford University Press: Oxford, 1997.
3. Scheiner S. Hydrogen Bonding. A Theoretical Perspective. Oxford University Press: Oxford, 1997.
4. Desiraju GR, Steiner T. The Weak Hydrogen Bonding in Structural Chemistry and Biology. Oxford University Press: Oxford, 1999.
5. Krygowski TM, Cyrański MK, Czarnocki Z, Häfelinger G, Katritzky AR. Tetrahedron 2000; 56: 1783-1796.
6. Gordon MS, Jensen JH. Acc. Chem. Res. 1996; 29: 536-543.
7. Grabowski SJ. J. Phys. Org. Chem. 2004; 17: 18-31.
8. Sobczyk L. Ber. Bunsenges. Phys. Chem. 1998; 102: 377-383.
9. Legon AC, Millen DJ. Chem. Soc. Rev. 1987; 16: 467-498.
10. Grabowski SJ. J. Phys. Org. Chem. 2003; 16: 797-802.
11. Steiner T. Angew. Chem. Int. Ed. 2002; 41: 48-76.
12. Lippincott ER, Schroeder R. J. Chem. Phys. 1955; 23: 1099-1106.
13. Derrison JD, Smith PH. Acta Crystallogr., Sect. A 1978; 34: 842-853.
14. Pauling L. J. Am. Chem. Soc. 1947; 69: 542-553.
15. Johnston HS, Parr C. J. Am. Chem. Soc. 1962; 85: 2544-2556.
16. Krygowski TM, Kalinowski MK, Turowska-Tyrk I, Hiberty PC, Milart P, Silvestro A, Topsom RD, Daehne S. Struct. Chem. 1991; 2: 71-80.
17. Dziembowska T, Szczodrowska B, Krygowski TM, Grabowski SJ. J. Phys. Org. Chem. 1994; 7: 142-146.
18. Krygowski TM, Grabowski SJ, Anulewicz-Ostrowska R, Izdebski J, Fiertek D. Pol. J. Chem. 2002; 76: 129-135.
19. Ichikawa M. Acta Crystallogr., Sect. B 1978; 34: 2074-2080.
20. Ichikawa M. J. Mol. Struct. 2000; 552: 63-70.
21. Grabowski SJ. Tetrahedron 1998; 54: 10153-10160.
22. Gilli G, Bellucci F, Ferretti V, Bertolasi V. J. Am. Chem. Soc. 1989; 111: 1023-1028.
23. Gilli P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 1994; 116: 909-915.
24. Hammett LP. Physical Organic Chemistry, McGraw-Hill: New York, 1970.
25. Shorter J. Pure Appl. Chem. 1994; 66: 2451-2468.
26. Hansch C, Leo A, Taft WR. Chem. Rev. 1991; 91: 165-195.
27. Woźniak K, Krygowski TM, Kariuki B, Jones W. J. Mol. Struct. 1991; 248: 331-343.
28. Szatylowicz H, Krygowski TM. Pol. J. Chem. 2004; 78: 1719-1731.
29. The Cambridge Structure Database, version 5.24, November 2002, updated July 2003.
30. Jin Z-M, Pan Y-J, Xu D-J, Xu Y-Z. Acta Crystallogr., Sect. C 2000; 56: e69-e70.
31. Watson WH, Vögtle F, Müller WM. J. Inclus. Phenom. Macrocycl. Chem. 1988; 6: 491-505.
32. Moreno-Fuquen R, de Almeida Santos RH, Lechat JR. J. Crystallogr. Spectrosc. Res. 1992; 22: 201-204.
33. Moreno-Fuquen R, de Almeida Santos RH, Francisco RHP. Acta Crystallogr., Sect. C 1998; 54: 513-515.
34. Kulkarni GU, Kumaradhas P, Rao CNR. Chem. Mater. 1998; 10: 3498-3505.
35. Filarowki A, Koll A, Glowiak T. J. Chem. Cryst. 1997;27:707-719.
36. Ng SW, Naumov P, Chantrapromma S, Raj SSS, Fun HK, Ibrahim AB, Wojciechowski G, Brzezinski B. J. Mol. Struct. 2001; 562: 185-196.
37. Etter MC, Reutzel SM. J. Am. Chem. Soc. 1991; 113: 2586-2598.
38. Moreno-Fuquen R, do Prado Gambardella MT, de Almeida Santos RH. Acta Crystallogr., Sect. C 1996; 52: 1745-1747.
39. Takahashi I, Takahashi M, Morita T, Keumi T, Kitajima H, Wagi M, Hatanaka M, Ohta T, Hosoi S. Anal. Sci. 2002; 18: 619-620.
40. Xiong Y, An T-C, He C, Liu Y, Chen J, Zha CH, Karlsson HT, Chen X. J. Chem. Cryst. 2002; 32: 219-225.
41. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
42. Bürgi HB, Dunitz JD. Structure Correlation. VCH: Weinheim, 1994; vol. 1, Chapt. 1-4 and vol. 2, Chapt. 11.
43. Abkowicz-Bienko AJ, Latajka Z. J. Phys. Chem. 2000; 104: 1004-1008.