Preferential deprotonation and conformational stability of dicarboxylic acids: A packing effect

Journal of Molecular Structure

Volumn 875, Issue 1-3, 2008, Pages 329-338

  Barooah, Nilotpal ^a   Singh, W Marjit ^a   Baruah, Jubaraj B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Conformers; Crystal structures; Deprotonation; Dicarboxylic acids; Hydrogen bonding

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DEPROTONATION; HYDROGEN BONDS; NITROGEN COMPOUNDS;

CONFORMERS; DICARBOXYLIC ACIDS; HETEROCYCLIC COMPOUNDS; PACKING EFFECTS; QUINOLINES;

CARBOXYLIC ACIDS;

EID: 39749127847     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2007.05.008     Document Type: Article

References (30)

1. Pauling L. The Nature of the Chemical Bonds. 2nd ed. (1948), Cornell University Press, Ithaca, NY
2. Hagler A.T., Leiserowitz L., and Tuyal M. J. Am. Chem. Soc. 98 (1976) 4600-4612
3. Etter M.C. Acc. Chem. Res. 23 (1990) 120-126
4. Nangia A., and Desiraju G.R. In: Weber E. (Ed). Supramolecular Synthons and Pattern Recognition: Design of Organic Solids (1998), Springer Verlag, Berlin
5. Almarsson O., and Zaworotko M.J. Chem. Commun. (2004) 1889-1896 and references therein
6. Bis J.A., and Zaworotko M.J. Crystal Growth Des. 5 (2005) 1169-1179
7. Chen H., Ogo S., and Fish R.H. J. Am. Chem. Soc. 118 (1996) 4993-5001
8. Rao C.N.R., Natarajan S., and Vaidhyanathan R. Angew. Chem., Int. Ed. 43 (2004) 1466-1496
9. Eddaoudi M., Moler D.B., Li H., Chen B., Reineke T.M., O'Keeffe M., and Yaghi O.M. Acc. Chem. Res. 34 (2001) 319-330
10. Eddaoudi M., Li H., and Yaghi O.M. J. Am. Chem. Soc. 127 (2005) 7110-7118
11. Tynan E., Jensen P., Lees A.C., Moubaraki B., Murray K.S., and Kruger P.E. Crystal Eng. Commun. 7 (2005) 90-95
12. Wang Z., Kravtsov V.C., and Zaworotko M.J. Angew Chem., Int. Ed. 44 (2005) 2877-2880
13. Sun D., Collins D.J., Ke Y., Zuo J.-L., and Zhou H.-C. Chem. Eur. J. 12 (2006) 3768-3776
14. Wang S.N., Xing H., Li Y.Z., Bai J.F., Bai J.F., Pan Y., Scheer M., and You X.Z. Eur. J. Inorg. Chem. (2006) 3041-3053
15. Evans O.R., and Lin W.B. Inorg. Chem. 39 (2000) 2189-2198
16. Mori W., Taamizawa S., Kato C.N., Ohmura T., and Sato T. Micropor. Mesopor. Mater. 73 (2004) 31-46
17. Fitzmaurice R.J., Kyne G.M., Douheret D., and Kilburn J.D. J. Chem. Soc. Perkin Trans. 1 (2002) 841-864
18. Ibragimov B.T., Izotova L.Y., Ashurov D.M., Weber E., and Talipov S.A. J. Struct. Chem. 46 (2005) S109-S115
19. Ishi-I T., Crego-Calama M., Timmerman P., Reihoudt D.N., and Shinkai S. Angew. Chem., Int. Ed. 41 (2002) 1924-1926
20. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), Wiley, Chichester
21. Walsh B.R.D., Bradner M.W., Fleischman S., Morales L.A., Moulton B., Rodriguez-Hornedo N., and Zaworotko M.J. Chem. Commun. (2003) 186-187
22. Oswald I.D.H., Allan D.R., McGregor P.A., Motherwell W.D.S., Parson S., and Pulham C.R. Acta Crystallogr. B B58 (2002) 1057-1066
23. Remanar J.F., Morissette S.L., Peterson M.L., Moulton B., MacPhee J.M., Guzman H.R., and Almarsson O. J. Am. Chem. Soc. 125 (2003) 8456-8457
24. Gung B.W., Patel M., and Xue X. J. Org. Chem. 70 (2005) 10532-10537
25. Sada K., Tani T., and Shinkai S. Synlett (2006) 2364-2374
26. Degenhardt III C.F., Lavin J.M., Smith M.D., and Shimizu K.D. Org. Lett. 7 (2005) 4079-4081
27. Kishikawa K., Iwashima C., Komoto S., Yamaguchi K., and Yamamoto K. J. Chem. Soc., Perkin Trans. 1 (2000) 2217
28. Barooah N., Sarma R.J., and Baruah J.B. Crystal Eng. Commun. 8 (2006) 608-615
29. Barooah N., Sarma R.J., Batsanov A.S., and Baruah J.B. J. Mol. Struct. 791 (2006) 122-130
30. Barooah N., Karmakar A., Sarma R.J., and Baruah J.B. Inorg. Chem. Commun. 9 (2006) 1251-1254