Revision of the structure and stereochemistry of the 2-naphthol-acetaldehyde 2:2 condensation product. A study by X-ray crystallography and the AM1 method

Journal of Physical Organic Chemistry

Volumn 14, Issue 4, 2001, Pages 210-216

  Rashidi Ranjbar, Parviz ^a   Mohajeri, Ali ^a   Mahmoudkhani, Amir Hossein ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

stacking; 2 Naphthol; Acetaldehyde; AM1 calculations; Condensation; Intramolecular hydrogen bonding; Phenols; X ray crystallography

Indexed keywords

EID: 0035310707     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.355     Document Type: Article

References (29)

1. Gardiner M, Raston C. Coord. Chem. Rev., 1997; 166: 1.
2. Bohmer V. Angew. Chem. 1995; 107: 785.
3. Shinkai S. Pure Appl. Chem. 1986; 58: 1523.
4. Iwamoto K, Araki K, Shinkai S. J. Org. Chem. 1991; 44: 3962.
5. Gutsche CD, Nam KC. J. Am. Chem. Soc. 1998; 110: 6153.
6. Poupelin JP, Saint-Ruf G, Lacroix R, Narcisse G, Foussand-Blangin O, Uchida-Ennouf G. Eur. J. Med. Chem. 1978; 13: 381.
7. Claisen L. Justus Liebigs Ann. Chem. 1887; 237: 271.
8. Van Allen JA, Gianini DD, Whitesides TH. 1982; J. Org. Chem. 47: 820.
9. Sirkecioglu O, Talinli N, Akar A. J. Chem. Res. (S) 1995; 502.
10. Diltey W, Steinborn H, J. Prakt. Chem. 1932; 133: 219.
11. Sirkecioglu O, Talinli N, Akar A. J. Heterocycl. Chem. 1998; 35: 457.
12. Zimmerman ASC, Zeng Z, Wu W, Reichert DE. J. Am. Chem. Soc. 1991; 113: 183.
13. Jeong KS, Tjivikua T, Muehidorf A, Deslongchamps G, Famulok M, Rebek J Jr. J. Am. Chem. Soc. 1991; 113: 201.
14. Hunter CA, Sanders JKM. J. Am. Chem. Soc. 1990; 112: 5525.
15. Jeffrey GA. An Introduction to Hydrogen Bonding. Oxford University Press: New York, 1997.
16. Dziewonski PM. Bull. Int. Acad. Polon. A 1933; 560.
17. Dewar MJS, Zeobish EG, Healy EF, Stewart JJP. J. Am. Chem. Soc. 1985; 107: 3902.
18. Cordes EH, Bull HG. Chem. Rev. 1974; 74: 581.
19. Jurek M, Spirko V, Kramerer WP. J. Mol. Spectrosc. 1997; 182: 364.
20. Anet FAL, Haq MZ. J. Am. Chem. Soc. 1965; 87: 3147.
21. Bushweller CH, Golini J, Rao GU, O'Neil JW. J. Am. Chem. Soc. 1970; 92: 3055.
22. Haasnoot CAG, de Leeuw FAAM, Altona C. Tetrahedron 1980; 36: 2783.
23. SMART and SAINT: Area Detector Control and Integration Software. Siemens Analytical X-ray Instruments: Madison, WI, 1995.
24. Sheldrick GM. SADABS: Program for Empirical Absorption Correction of Area Detectors. University of Göttingen: Göttinga, 1996.
25. Blessing RH. Acta Crystallogr., Sect. A 51: 1995; 33.
26. SHELXTL (Version 5.10). Bruker AXS: Madison, WI, 1997.
27. Stewart JJP. QCPE 581, 1990. Department of Chemistry, Indiana University: Bloomington, IN.
28. Hirst DM. A Computational Approach to Chemistry. Blackwell Scientific: Oxford, 1990.
29. Rashidi-Ranjbar P, Najafpour J, Piri F. J. Phys. Org. Chem. 1998; 11: 781.