Abstract
Reaction of symmetrical and unsymmetrical (thio)barbituric acids with aldehydes in the presence of triethylamine afforded a new form of bis-(thio)barbiturate containing charge-separated inter- and eight-membered intramolecular H-bonds. The reaction products were obtained as bis-(thio)barbiturates containing eight-membered intramolecular H-bond in the presence of l-(+)-tartaric acid (TA). The intramolecular H-bond strength (kcal/mol) and corresponding pKa value for 4ab′ were estimated to be 37 kcal/mol and −1.3, respectively.
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M. Nishio, Tetrahedron 61, 6923–6950 (2005)
X.-B. Wang, H. K Woo, B. Kira, L.-S. Wang. Angew. Chem. Int. Ed. 44, 4968–4972 (2005)
R.M. McKinlay, P.K. Thallapally, G.W.V. Cave, J.L. Atwood, Angew. Chem. Int. Ed. 44, 5733–5736 (2005)
H. Gong, M.J. Krische, J. Am. Chem. Soc. 127, 1719–1725 (2005)
A. Tessa ten Cate, P.Y.W. Dankers, R.P. Sijbesma, E.W. Meijer, J. Org. Chem. 70, 5799-5803 (2005)
P. Prabhakaran, V.G. Puranik, G.J. Sanjayan, J. Org. Chem. 70, 10067–10072 (2005)
I. Azumaya, D. Uchida, T. Kato, A. Yokoyama, A. Tanatani, H. Takayanagi, T. Yokozawa, Angew. Chem. Int. Ed. 43, 1360–1363 (2004)
Y. Zhu, D.G. Drueckhammer, J. Org. Chem. 70, 7755–7760 (2005)
C.P. Price, A.J. Matzger, J. Org. Chem. 70, 1–6 (2005)
X. Zhang, H. Du, Z. Wang, Y.-D. Wu, K. Ding, J. Org. Chem. 71, 2862–2869 (2006)
I. Alfonso, M.I. Burguete, S.V. Luis, J. Org. Chem. 71, 2242–2250 (2006)
M.H. Abraham, R.J. Abraham, J. Byrne, L. Griffiths. J. Org. Chem. 71, 3389–3394 (2006)
G.A. Jeffery, W. Saenger, Hydrogen bonding in biological structures (Springer-Verlag, Berlin, Germany, 1991)
A.M. Asiri, S.A. Khan, S.W. Ng, Acta Cryst. Sect. E. 65, o1860–o1861 (2009)
Y. Zhang, C.-S. Wang, J. Comput. Chem. 30, 1251–1260 (2009)
Y.-D. Wu, K.W.K. Chan, D.-P. Wang, J. Am. Chem. Soc. 118, 9794–9795 (1996)
D. Yang, J. Qu, B. Li, F.-F. Ng, X.-C. Wang, K.-K. Cheung, D.-P. Wang, Y.-D. Wu, J. Am. Chem. Soc. 121, 589–590 (1999)
A. G. J. Ligtenbarg, R. Hage, A. Meetsma, B. L. Feringa, J. Chem. Soc., Perkin Trans. 2, 807–812 (1999)
C. Peter, X. Daura, W.F. van Gunsteren, J. Am. Chem. Soc. 122, 7461–7466 (2000)
N. Noroozi Pesyan, M. Jalilzadeh, Turk. J. Chem. 36, 788–804 (2012)
G. Gilli, P. Gilli, J. Mol. Struct. 552, 1–15 (2000)
P. Gilli, V. Bertolasi, L. Pretto, V. Ferretti, G. Gilli, J. Am. Chem. Soc. 126, 3845–3855 (2004)
D. Neumann, “The Design and Synthesis of Novel Barbiturates of Pharmaceutical Interest”. University of New Orleans Theses and Dissertations. Paper 1040 (2004) http://scholarworks.uno.edu/td
A.I. Vogel, A.R. Tatchell, B.S. Furnis, A.J. Hannaford, P.W.G. Smith, Vogel's textbook of practical organic chemistry, 5th edn. (Longman, UK, 1989)
B.S. Jursic, D.M. Neumann, K.L. Martin, E.D. Stevens, Org. Lett. 4, 811–813 (2002)
B.S. Jursic, D.M. Neumann, Z. Moore, E.D. Stevens, J. Org. Chem. 67, 2372–2374 (2002)
B.S. Jursic, J. Heterocycl. Chem. 40, 167–170 (2003)
J. Adamson, B.J. Coe, H.L. Grassam, J.C. Jeffery, S.J. Coles, M.B. Hursthouse, J. Chem. Soc. Perkin Trans. 1, 2483–2488 (1999)
M. Jalilzadeh, N. Noroozi Pesyan, F. Rezaee, S. Rastgar, Y. Hosseini, E. Şahin, Mol. Divers. 15, 721–731 (2011)
M. Jalilzadeh, N. Noroozi Pesyan, Bull. Korean Chem. Soc. 32, 3382–3388 (2011)
M. Jalilzadeh, N. Noroozi Pesyan, J. Korean Chem. Soc. 55, 940–951 (2011)
N. Noroozi Pesyan, M. Jalilzadeh, J. Chem. Sci. Tech. (JCST) 1, 1–8 (2012)
N. Noroozi Pesyan, S. Rastgar, Y. Hosseini, Acta Cryst. Sect E. 65, o1444 (2009)
Y. Hosseini, S. Rastgar, Z. Heren, O. Büyükgüngör, N. Noroozi Pesyan, J. Chin. Chem. Soc. 58, 309–318 (2011)
M.N. Elinson, A.N. Vereshchagin, N.O. Stepanov, P.A. Belyakov, G.I. Nikishin, Tetrahedron Lett. 51, 6598–6601 (2010)
R.L. Schriner, R.C. Fusan, D.Y. Curtin, T.C. Morrill, The systematic identification of organic compounds, 6th edn. (Wiley, New York, 1980)
G. A. Jeffrey, An Introduction to Hydrogen Bonding (Oxford University Press, Oxford, 1997)
T. Steiner, Angew. Chem. Int. Ed. 41, 48–76 (2002)
T.K. Harris, Q. Zhao, A.S. Mildvan, J. Mol. Struct. 552, 97–109 (2000)
D. Kalaivani, R. Malarvizhi, Acta Cryst. Sect. E. 65, o2548 (2009)
E.V. Anslyn, D.A. Dougherty, Modern Physical Organic Chemistry. Sausalito, CA: University Science Books, ISBN 1-891389-31-9 (2006)
J.-C. Wallet, E. Molins, C. Miravitlles, J. Phys. Org. Chem. 11, 751–755 (1998)
J.C. Wallet, E. Molins, C. Miravitlles, Struct. Chem. 11, 319–323 (2000)
E. Espinosa, E. Molins, J.-C. Wallet, J. Phys. Org. Chem. 12, 499–502 (1999)
H.A. Dabbagh, N. Noroozi Pesyan, B.O. Patrick, B.R. James, Can. J. Chem. 82, 1179–1185 (2004)
J. Chen, M.A. McAllister, J.K. Lee, K.N. Houk, J. Org. Chem. 63, 4611–4619 (1998)
N. Noroozi Pesyan, Magn. Reson. Chem. 47, 953–958 (2009)
P. Gregory, Dyes Pigment. 7, 45–56 (1986)
Rigaku/MSC, Inc., 9009 new Trails Drive, The Woodlands, TX 77381
G.M. Sheldrick, SHELXS97 and SHELXL97 (University of Göttingen, Germany, 1997)
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We gratefully acknowledge the financial support by the Research Council of Urmia University.
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Full characterization data for compounds 3cd′–3fd′, 4ab′–4ae′ and crystallographic data for 4ab′ are available (PDF 7154 kb)
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Pesyan, N.N., Jalilzadeh, M., Torkaman, N.Y. et al. Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates. J IRAN CHEM SOC 11, 35–45 (2014). https://doi.org/10.1007/s13738-013-0273-x
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DOI: https://doi.org/10.1007/s13738-013-0273-x