Citation: LIU Dong-Jia, WANG Chang-Sheng. Effect of Substituents on Hydrogen Bond Strength in Hydrogen-Bonded N-methylacetamide and Uracil Complexes[J]. Acta Physico-Chimica Sinica doi: 10.3866/PKU.WHXB201209263 shu

Effect of Substituents on Hydrogen Bond Strength in Hydrogen-Bonded N-methylacetamide and Uracil Complexes

1.
School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning Province, P. R. China

Received Date: 27 July 2012
Available Online: 26 September 2012
Fund Project: 国家自然科学基金(20973088, 21173109,21133005) (20973088, 21173109,21133005)教育部高等学校博士点基金(20102136110001)资助项目 (20102136110001)

Theoretical calculations on a series of N－H…O＝C hydrogen-bonded complexes containing 1-methyluracil and N-methylacetamide were carried out using B3LYP and MP2 methods. Substituent effects in the hydrogen bond acceptor molecule (1-methyluracil) on the hydrogen bond strength and hydrogen bond cooperativity were explored. The calculation results show that electron donating groups shorten the H…O distance and strengthen the N－H…O＝C hydrogen bond, whereas electron withdrawing groups lengthen the H…O distance and weaken the N－H…O＝C hydrogen bond. Natural bond orbital (NBO) analysis further indicates that electron donating groups result in a larger positive charge on the H atom and a larger negative charge on the O atom in the N－H…O＝C bond, and result in increased charge transfer between the proton donor and acceptor molecules. Electron withdrawing groups show the opposite results. NBO analysis also indicates that electron donating groups result in larger second-order interaction energies between the oxygen lone pair and the N － H antibonding orbital when compared to the 1-methyluracil-containing complex (R=H), while electron withdrawing groups result in smaller second-order interaction energies.
- Hydrogen-bonded complex,
- Substituent,
- Hydrogen bond strength,
- Natural bond orbital analysis,
- Hydrogen bond cooperativity
1. [1]
  
  (1) Desiraju, G. R.; Steiner, T. The Weak of Hydrogen Bond;Oxford University Press: New Nork, 1999; pp 343-412.
2. [2]
  (2) Jeffrey, G. A. An Introduction to Hydrogen Bonding; OxfordUniversity Press: New York, 1997; pp 184-212.
3. [3]
  (3) Scheiner, S. Hydrogen Bonding: A Theoretical Perspective;Oxford University Press: New York, 1997; pp 105-117.
4. [4]
  (4) Chalaris, M.; Samios, J. J. Phys. Chem. B 1999, 103, 1161.doi: 10.1021/jp982559f
5. [5]
  (5) Mohajeri, A.; Nobandegani, F. F. J. Phys. Chem. A 2008, 112,281. doi: 10.1021/jp075992a
6. [6]
  (6) Sun, C. L.;Wang, C. S. Sci. China Ser. B-Chem. 2009, 39 (6),481. [孙长亮, 王长生. 中国科学B 辑: 化学, 2009, 39 (6),481.]
7. [7]
  (7) Jiang, X. N.;Wang, C. S. ChemPhysChem 2009, 10, 3330.doi: 10.1002/cphc.200900591
8. [8]
  (8) Li, Y.; Jiang, X. N.;Wang, C. S. J. Comput. Chem. 2011, 32,953. doi: 10.1002/jcc.v32.5
9. [9]
  (9) Kolew, S. K.; Petkow, P. S.; Rangelow, M. A.; Vayssilow, G. N.J. Phys. Chem. A 2011, 115, 14054. doi: 10.1021/jp204313f
10. [10]
  (10) Angelina, E. L.; Peruchena, N. M. J. Phys. Chem. A 2011, 115,4701. doi: 10.1021/jp1105168
11. [11]
  (11) Ji, C. G.; Zhang, Z. H. J. Phys. Chem. B 2011, 115, 12230. doi: 10.1021/jp205907h
12. [12]
  (12) Iz rodina, E. I.; MacFarlane, D. R. J. Phys. Chem. B 2011,115, 14659. doi: 10.1021/jp208150b
13. [13]
  (13) Dong, H.; Hua,W. J.; Li, S. H. J. Phys. Chem. A 2007, 111,2941.
14. [14]
  (14) Vargas, R.; Garza, J.; Friesner, R. A.; Stern, H.; Hay, B. P.;Dixon, D. A. J. Phys. Chem. A 2001, 105, 4963. doi: 10.1021/jp003888m
15. [15]
  (15) Kawahara, S.; Kobori, A.; Sekine, M.; Taira, K.; Uchimaru, T.J. Phys. Chem. A 2001, 105, 10596. doi: 10.1021/jp0124645
16. [16]
  (16) Kawahara, S.; Uchimaru, T.; Taira, K.; Sekine, M. J. Phys. Chem. A 2001, 105, 3894.
17. [17]
  (17) Sun, C. L.; Zhang, Y.; Jiang, X. N.;Wang, C. S.; Yang, Z. Z. Sci. China Ser. B-Chem. 2008, 38 (9), 762. [孙长亮, 张艳, 姜笑楠, 王长生, 杨忠志. 中国科学B 辑: 化学, 2008, 38 (9), 762.]
18. [18]
  (18) Sun, C. L.; Jiang, X. N.;Wang, C. S. J. Comput. Chem. 2009,30, 2567. doi: 10.1002/jcc.v30:15
19. [19]
  (19) Wang, C. S.; Zhang, Y.; Gao, K.; Yang, Z. Z. J. Chem. Phys.2005, 123, 024307. doi: 10.1063/1.1979471
20. [20]
  (20) Zhang, Y.;Wang, C. S. J. Comput. Chem. 2009, 30, 1251. doi: 10.1002/jcc.v30:8
21. [21]
  (21) Sun, C. L.;Wang, C. S. J. Mol. Struct. -Theochem 2010, 956, 38.doi: 10.1016/j.theochem.2010.06.020
22. [22]
  (22) Jiang, X. N.; Sun, C. L.;Wang, C. S. J. Comput. Chem. 2010,31, 1410.
23. [23]
  (23) Chen, Y. F.; Dannenberg, J. J. J. Am. Chem. Soc. 2006, 128,8100. doi: 10.1021/ja060494l
24. [24]
  (24) Nobko, N.; Dannenberg, J. J. J. Phys. Chem. A 2003, 107, 6688.doi: 10.1021/jp0345497
25. [25]
  (25) Nobko, N.; Dannenberg, J. J. J. Phys. Chem. A 2003, 107,10389.
26. [26]
  (26) Zhao, Y. L.;Wu, Y. D. J. Am. Chem. Soc. 2002, 124, 1570. doi: 10.1021/ja016230a
27. [27]
  (27) Wu, Y. D.; Zhao, Y. L. J. Am. Chem. Soc. 2001, 123, 5313. doi: 10.1021/ja003482n
28. [28]
  (28) Tan, H.W.; Qu,W.W.; Chen, G. J.; Liu, R. Z. J. Phys. Chem. A2005, 109, 6303. doi: 10.1021/jp051444q
29. [29]
  (29) Hunter, K. C.; Millen, A. L.;Wetmore, S. D. J. Phys. Chem. B2007, 111, 1858. doi: 10.1021/jp066902p
30. [30]
  (30) Jeong, E.; Kim, H.; Lee, S.W.; Han, K. Mol. Cells 2003, 16,161.
31. [31]
  (31) Cheng, A. C.; Frankel, A. D. J. Am. Chem. Soc. 2004, 126, 434.doi: 10.1021/ja037264g
32. [32]
  (32) Tkachenko, M. Y.; Boryskina, O. P.; Shestopalova, A. V.;Tolstorukov, M. Y. Int. J. Quantum Chem. 2010, 110, 230. doi: 10.1002/qua.v110:1
33. [33]
  (33) Frish, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gassian 03,Revision D.01; Gaussian Inc.: Pittsburgh, PA, 2003.
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