Services on Demand
Article
Indicators
Related links
- Cited by Google
- Similars in Google
Share
South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
S.Afr.j.chem. (Online) vol.64 Durban 2011
RESEARCH ARTICLE
Part II: Ab initio and NMR investigations into the barrier to internal rotation of various oxo- and thio- analogues of 2-Oxo-2H-chromen-7-yl dimethylcarbamates
Caryl K.A. Janse van Rensburg; Ross S. Robinson*; Hendrik G. Kruger
Warren Research Laboratory, School of Chemistry, University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg, 3209 South Africa
ABSTRACT
A range of 2-oxo-2H-chromen-7-yl dimethylcarbamates were synthesized as described in part I of this publication, containing either an oxygen or sulphur a to the carbonyl or thiocarbonyl group of the amide moiety. Variable temperature and exchange spectroscopy NMR was performed on these compounds and the barrier to free amide rotation was calculated. Each of these compounds were also modelled ab initio and the gas phase barrier to rotation calculated. These three sets of data were compared and the influence of the a-heteroatom on rotation for amides and thioamides evaluated.
Keywords: Thiocarbonyl, amide, rotational barrier
Full text available only in pdf format.
References
1 K.E. Laidig and L.M. Cameron, J . Am. Chem. Soc., 1996, 118, 1737-1742 [ Links ]
2 C.R. Kemnitz and M.J. Loewen, J. Am. Chem. Soc., 2007, 129, 2521-2528. [ Links ]
3 J.S. Craw, I.H. Hillier, G.A. Morris and M.A. Vincent, Mol. Phys., 1997, 92, 421. [ Links ]
4 F.J. Luque andM. Orozco,J. Chem. Soc., Perkin Trans. 2, 1993, 683-690. [ Links ]
5 H. Lee, M. Lee, Y. Choi, H. Park and K. Lee, J. Mol. Struct.: THEOCHEM, 2003, 631, 101. [ Links ]
6 H. Basch and S. Hoz, Chemical Physics Letters, 1998, 294, 117. [ Links ]
7 R.N. Salvatore, F. Chu, A.S. Nagale, E.A. Kapxhiu, R.M. Cross and K.W. Jung, Tetrahedron, 2002, 58, 3329-3347. [ Links ]
8 D. Kaur, J. Mol. Struct.: THEOCHEM, 2005, 757, 149-153. [ Links ]
9 J.H. Wynne, S.D. Jensen and A.W. Snow, J. Org. Chem, 2003, 68, 3733-3735. [ Links ]
10 M. Koketsu, Y. Fukuta and H. Ishihara, J. Org. Chem., 2002, 67, 1008-1011. [ Links ]
11 M. Feroci, M.A. Casadei, M. Orsini, L. Palombi and A. Inesi, J. Org. Chem., 2003, 68, 1548-1551. [ Links ]
12 F.J. Luque and M. Orozco, J. Chem. Soc. Perkin Trans. 2, 1993, 683-690. [ Links ]
13 L. Pauling, Proc. R. Soc. Lond. A., 1977, 356, 433-441. [ Links ]
14 K.B. Wiberg and K.E. Laidig, J. Am. Chem. Soc., 1987, 109, 5935-5943. [ Links ]
15 K.B.WibergandC.M.Breneman, J.Am. Chem. Soc., 1992, 114,831-840. [ Links ]
16 K.B. Wiberg and R. Glaser, J. Am. Chem. Soc., 1992, 114, 841-850. [ Links ]
17 K.B. Wiberg and P.R. Rablen, J. Am. Chem. Soc., 1995, 117, 2201-2209. [ Links ]
18 K.B. Wiberg and D.J. Rush, J. Am. Chem. Soc., 2001, 123, 2038. [ Links ]
19 D. Lauvergnat and P.C. Hiberty, J. Am. Chem. Soc., 1997, 119, 9478-9482. [ Links ]
20 P.V. Bharatam, R. Moudgil and D. Kaur, J. Phys. Chem. A, 2003, 107, 1627-1634. [ Links ]
21 K.B. Wiberg, P.R. Rablen, D.J. Rush and T.A. Keith, J. Am. Chem. Soc., 1995, 117, 4261. [ Links ]
22 T. Drakenberg, K. Dahlqvist and S. Forsen, J. Phys. Chem., 1972, 76, 2178. [ Links ]
23 D. Kaur, P. Sharma, P.V Bharatam and N. Dogra, J. Mol. Struct.: THEOCHEM, 2006, 759, 41-49. [ Links ]
24 C. Cox, T. Lectka, J. Org. Chem., 1998, 63, 2426. [ Links ]
25 Y. Otani, O. Nagae, Y. Naruse, S. Inagaki, M. Ohno, K. Yamaguchi, G. Yamamoto, M. Uchiyama, T. Ohwada, J. Am. Chem. Soc., 2003, 125, 15191-15199. [ Links ]
26 B. Galabov, S. Ilieva, B. Hadjieva, E. Dinchova, J. Phys. Chem. A, 2003, 107, 5854-5861. [ Links ]
27 C. Piccinni-Leopardi, O. Fabre, D. Zimmermann and J. Reisse, Can. J. Chem., 1977, 55, 2649-2655. [ Links ]
28 R.J. Smith, D.H. Williams and K. James, Chem. Commun., 1989, 682-683. [ Links ]
29 E.A. Basso, P.R. Oliveira, F. Wiectzycoski, R.M. Pontes and B.C. Fiorin, J. Mol. Struct. 2005, 753, 139-146. [ Links ]
30 D.G. Gehring, W.A. Mosher and G.S. Reddy, J. Org. Chem., 1966, 31, 3436-3437. [ Links ]
31 D. Kost and H. Egozy, Journal of Organic Chemistry, The, 1989, 54, 4909. [ Links ]
32 B.J. Wik, M. Lersch, A. Krivokapic and M. Tilset, J. Am. Chem. Soc., 2006, 128, 2682-2696. [ Links ]
33 A. Anand, A.D. Roy, R. Chakrabarty, A.K. Saxena and R. Roy, Tetrahedron, 2007, 63, 5236-5243. [ Links ]
34 T. Ayama, H. Sakane, T. Muneishi and T. Hirao, Chem. Commun., 2008, 765-767. [ Links ]
35 I. Pianet and J.M. Vincent, Inorg. Chem, 2004, 43, 2947-2953. [ Links ]
36 H.C. Bushweller, J.W. O'Neil, M.H. Halford and F.H. Bissett, J. Am. Chem. Soc., 1971, 93, 1471-1473. [ Links ]
37 S.A. Matchett, G. Zhang and D. Frattarelli, Organometallics, 2004, 23, 5440-5449. [ Links ]
38 R. Singh and G.M. Whitesides, J. Am. Chem. Soc., 1990, 112, 1190-1197. [ Links ]
39 R. Quintanilla-Licea, J.F. Colunga-Valladares, A. Caballero-Quintero, C. Rodriguez-Padilla, R. Tamez-Guerra, R. Gomez-Flores and N. Waksman, Molecules, 2002, 7, 662-673. [ Links ]
40 D.J. Clarke, Synthetic and Spectroscopic Studies of Isopsoralen Derivatives, M.Sc. thesis, University of Natal, Pietermaritzburg South Africa, 2001. [ Links ]
41 D.J. Clarke and R.S. Robinson, Tetrahedron, 2002, 58, 2831-2837. [ Links ]
42 J.C. Cobas and M, Martin-Pastor, MestReC, 2004. [ Links ]
43 C.K.A. Janse van Rensburg and R.S. Robinson, S. Afr. J. Chem., 2009, 62, 143-148. [ Links ]
44 J.W. Ochterski, in http://www.gaussian.com/g_whitepap/white_pap.htm, 2000. [ Links ]
45 E.D. Glendening and J.A. Hrabal, J. Am. Chem. Soc., 1997, 119, 12940-12946. [ Links ]
46 N.G. Vassilev and VS. Dimitrov, J. Mol. Struct, 2003, 654, 27-34. [ Links ]
47 Y. Mo, P. von Rague Schleyer, W. Wu, M. Lin and Q. Zhang, J. Gao, J. Phys. Chem. A, 2003, 107, 10011-10018. [ Links ]
48 C.H. Yoder and R.D. Gardner, J. Org. Chem., 1981, 46, 64-66. [ Links ]
49 R.C. Weast, Handbook of Chemistry and Physics, 63rd Edn; Boca Raton: Florida, 1984. [ Links ]
50 G.M. Sheldrick, in SHELXS-97, Program for Solution of Crystal Structures, University of Gottingen, Germany, 1997. [ Links ]
51 L.J. Farrugia, In ORTEP 3 for Windows, V1.01 beta, Department of Chemistry, University of Glasgow, Scotland, 1998. [ Links ]
52 EXSYCalc, is available for free download from Mestrelab research. [ Links ]
53 Gaussian 03, Version 6.0, 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. Gonzalez and J.A. Pople, Gaussian, Inc., Pittsburgh. [ Links ]
Received 13 December 2010
Revised 15 February 2011
Accepted 20 June 2011
Submitted by invitation to celebrate 2011 the 'International Year of Chemistry'.
* E-mail: robinsonr@ukzn.ac.za