A study in desmotropy

Solid State Nuclear Magnetic Resonance

Volumn 34, Issue 1-2, 2008, Pages 68-76

  Holzer, Wolfgang ^a   Claramunt, Rosa Ma ^b   López, Concepción ^b   Alkorta, Ibon ^c   Elguero, José ^c  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Desmotropy; GIAO calculations; Pyrazolinones; Solid state NMR; Tautomerism

Indexed keywords

DESMOTROPY; GIAO CALCULATIONS; PYRAZOLINONES; SOLID-STATE NMR; TAUTOMERISM;

EID: 51749114672     PISSN: 09262040     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ssnmr.2007.12.002     Document Type: Article

References (61)

1. Jacobson P. Chem. Ber. 21 (1888) 2624-2631 (stated on p. 2628)
2. Baither O. Chem. Ber. 20 (1887) 1731-1739 (refers to P. Jacobson)
3. Dunitz J.D. X-ray Analysis and the Structure of Organic Molecules (1979), Cornell University Press, Ithaca
4. In: Desiraju G.R. (Ed). Organic Solid State Chemistry (1987), Elsevier, Amsterdam
5. Desiraju G.R. Crystal Engineering (1989), Elsevier, Amsterdam
6. In: Bürgi H.-B., and Dunitz J.D. (Eds). Structure Correlation (1994), VCH, Weinheim (two volumes)
7. Bernstein J. Polymorphism in Molecular Crystals (2002), Clarendon Press, Oxford (but the example of Desiraju desmotropy of 1983 [3], is reported on p. 84)
8. Desiraju G.R., and Chem. Soc. J. Perkin Trans. 2 (1983) 1025-1030
9. Bechtel F., Gaultier J., and Hauw C. Cryst. Struct. Commun. 3 (1973) 469-472
10. Halcrow M.A., Powell H.R., and Duer M.J. Acta Crystallogr. Section B 52 (1996) 746-752
11. Foces-Foces C., Fontenas C., Elguero J., and Sobrados I. An. Quím. Int. Ed. 93 (1997) 219-224
12. Kubicki M. Acta Crystallogr. Section B 60 (2004) 191-196
13. Lempert K., Nyitrai J., Sohár P., and Zauer K. Tetrahedron Lett. (1964) 2679-2684
14. Lempert K., Nyitrai J., and Sohár P. Tetrahedron Lett. (1965) 1795-1799
15. Nyitrai J., and Lempert K. Tetrahedron 25 (1969) 4265-4275
16. Nyitrai J., and Lempert K. Acta Chim. Acad. Sci. Hung. 73 (1972) 43-61
17. Lempert K., Nyitrai J., Zauer K., Kálmán A., Argay Gy., Duisenberg A.J.M., and Sohár P. Tetrahedron 29 (1973) 3565-3569
18. Sala L.F., Martell A.E., Motekaitis R.J., and Abbott E.H. Inorg. Chim. Acta 135 (1987) 123-127
19. Foces-Foces C., Llamas-Saiz A.L., Claramunt R.M., López C., and Elguero J. J. Chem. Soc. Chem. Commun. (1994) 1143-1145
20. Casas J.S., Castellano E.E., Macías A., Playá N., Sánchez A., Sordo J., Varela J.M., and Zukerman-Schpector J. Inorg. Chim. Acta 238 (1995) 129-137
21. Boldt P., Zippel S., and Ratkowsky M. J. Chem. Soc. Perkin Trans. 1 (1996) 2615-2617
22. Bauer M., Harris R.K., Rao R.C., Apperley D.C., and Rodger C.A. J. Chem. Soc. Perkin Trans. 2 (1998) 475-481
23. Aronova E.B., and Ginak A.I. Russ. J. Gen. Chem. 71 (2001) 1605-1607
24. García M.A., López C., Claramunt R.M., Kenz A., Pierrot M., and Elguero J. Helv. Chim. Acta 85 (2002) 2763-2776
25. Aronova E.B., and Ginak A.I. Russ. J. Appl. Chem. 75 (2002) 1885-1886
26. Aranyi P., et al. Sanofi-Aventis, PCT WO 2005009969. Chem. Abstr. 142 (2005) 197895
27. Finta Z., et al. Sanofi-Aventis, PCT WO 2005100320. Chem. Abstr. 143 (2005) 410963
28. Willstätter R., and Wheeler A.S. Chem. Ber. 47 (1914) 2796-2801
29. Madinaveitia A., and Olay E. An. Soc. Esp. Fis. Quim. 31 (1933) 134-138
30. Thomson R.H. Q. Rev. Chem. Soc. 10 (1956) 27-43
31. Forsén S., and Nilsson M. In: Zabicky J. (Ed). The Chemistry of the Carbonyl Group vol. 2 (1970), Interscience, Wiley, London 168-183
32. Elguero J., Marzin C., Katritzky A.R., and Linda P. The Tautomerism of Heterocycles (1976), Academic Press, New York
33. Minkin V.I., Garnovskii A.G., Elguero J., Katritzky A.R., and Denisko O.V. Adv. Heterocycl. Chem. 76 (2000) 157-323
34. Dardonville C., Elguero J., Rozas I., Fernández-Castaño C., Foces-Foces C., and Elguero J. New J. Chem. 22 (1998) 1421-1430
35. Sanz D., Claramunt R.M., Alkorta I., and Elguero J. Struct. Chem. 18 (2007) 703-708
36. Heinisch G., Hollub C., and Holzer W. J. Heterocycl. Chem. 28 (1991) 1047-1050
37. Guard J.A.M., and Steel P.J. Aust. J. Chem. 47 (1994) 1453-1459
38. Akama Y., Shiro M., Ueda T., and Kajitani M. Acta Crystallogr. Section C 51 (1995) 1310-1314
39. Akama Y., Tong A., Matsumoto N., Ikeda T., and Tanaka S. Vib. Spectrosc. 13 (1996) 113-115
40. Dunitz J.D. Chem. Commun. (2003) 545-548
41. Day G.M., Motherwell W.D.S., Ammon H.L., Boerrigter S.X.M., Della Valle R.G., Venuti E., Dzyabchenko A., Dunitz J.D., Schweizer B., van Eijck B.P., Erk P., Facelli J.C., Bazterra V.E., Ferraro M.B., Hofmann D.W.M., Leusen F.J.J., Liang C., Pantelides C.C., Karamertzanis P.G., Price S.L., Lewis T.C., Nowell H., Torrisi A., Scheraga H.A., Arnautova Y.A., Schmidt M.U., and Verwer P. Acta Crystallogr. B 61 (2005) 511-527
42. Holzer W., Mereiter K., and Plagens B. Heterocycles 50 (1999) 799-818
43. Blanco F., Alkorta I., and Elguero J. Magn. Reson. Chem. 45 (2007) 797-800
44. Claramunt R.M., López C., García M.A., Denisov G.S., Alkorta I., and Elguero J. New J. Chem. 27 (2003) 734-742
45. López C., Claramunt R.M., García M.A., and Elguero J. Central Eur. J. Chem. 2 (2004) 660-671
46. Marchetti F., Pettinari C., Cingolani A., Lobbia G.G., Cassetta A., and Barba L. J. Organomet. Chem. 517 (1996) 141-154
47. Sarenko A.S., Ya. Kvitko I., and Efros L.S. Chem. Heterocycl. Comp. (1972) 722-727
48. Wise L.D., Butler D.E., DeWald H.A., Lustgarten D.M., Pattison I.C., Schweiss D.N., Coughenour L.L., Downs D.A., Heffner T.G., and Pugsley T.A. J. Med. Chem. 30 (1987) 1807-1812
49. Holzer W., Claramunt R.M., Pérez-Torralba M., Guggi D., and Brehmer T.H. J. Org. Chem. 68 (2003) 7943-7950
50. Holzer W., and Krca I. Heterocycles 60 (2003) 2323-2342
51. Holzer W., and Hahn K. J. Heterocycl. Chem. 40 (2003) 303-314
52. Jensen B.S. Acta Chem. Scand. 13 (1959) 1668-1670
53. Singh P., Paul K., and Holzer W. Bioorg. Med. Chem. 14 (2006) 5061-5071
54. Berger S., and Braun S. 200 and more Basic NMR Experiments (2004), Wiley-VCH, Weinheim, Germany
55. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
56. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
57. Ditchfield R., Hehre W.J., and Pople J.A. J. A. J. Chem. Phys. 54 (1971) 724-728
58. Frisch M.J., Pople J.A., Krishnam R., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265-3269
59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C.
60. Ditchfield R. Mol. Phys. 27 (1974) 789-807
61. London F. J. Phys. Radium 8 (1937) 397-409