Preliminary approach to estimation and prediction of infrared spectroscopy for Mannich bases by atomic electronegativity distance vector (VAED)

Computational Biology and Chemistry

Volumn 27, Issue 3, 2003, Pages 229-239

  Liao, Chunyang ^a   Chen, Zhitao ^a   Yin, Zihui ^a   Li, Shengshi Z ^a  

^a CHONGQING UNIVERSITY   (China)

Author keywords

Atomic electronegativity distance vector (VAED); Infrared spectroscopy (IR); Mannich base; Molecular modeling; Quantitative structure spectrum relationship (QSSR); Vibration frequency

Indexed keywords

COMPUTER SIMULATION; CORRELATION METHODS; MOLECULAR STRUCTURE; REGRESSION ANALYSIS; VECTORS;

ATOMIC ELECTRONEGATIVITY DISTANCE VECTORS;

INFRARED SPECTROSCOPY;

EID: 0042730048     PISSN: 14769271     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0097-8485(02)00056-6     Document Type: Article

References (38)

1. Anker L.S., Jurs P.C. Prediction of carbon-13 nuclear magnetic resonance chemical shifts by artificial neural networks. Anal. Chem. 64:1992;1157-1164.
2. Balaban A.T. High discrimination distance-based topological index. Chem. Phys. Lett. 89:1982;399-404.
3. Balaban A.T. Topological indexes based on topological distance in molecular graphs. Pure Appl. Chem. 55:1983;199-206.
4. Benigni R., Passcrini L., Livingstone D.J., Johnson M.A., Giuliani A. Infrared spectra information and their correlation with QSAR descriptors. J. Chem. Inf. Comput. Sci. 39:1999;558-562.
5. Benigni R., Giuliani A., Passerini L. Infrared spectra as chemical descriptors for QSAR models. J. Chem. Inf. Comput. Sci. 41:(3):2001;727-730.
6. Bonchev D., Trinajstic N. A new approach in ecoloxicolgical studies. J. Chem. Phys. 67:1977;4517.
7. Bursi R., Dao T., van Wijk T., de Gooyer M., Kellenbach E., Verwer P. Comparative spectra analysis (CoSA): spectra as threedimensional molecular descriptors for the prediction of biological activities. J. Chem. Inf. Comput. Sci. 39:1999;861-867.
8. Chen H.L., Zou J.H. The Mannich reaction among p-methoxyacctophenone benzaldehyde or p-methoxybenzaldehyde and arylamines. J. Southwest Chin. Norm. Univ. (Nat. Sci.). 24:(2):1999;190-195. in Chinese.
9. Chen R.Y., Feng K.S., Liu X.I., Sun M., Miu P.M. Synthesis of 3,4-diphenyl-4-oxo-l,3-dinitrogen-4-phosphorus-hetero-2-cyclopentanone through analogous Mannich reaction and its structural analysis. Sci. Chin. Series B-Chem. 8:1992;785-791. in Chinese.
10. Clouser D.L., Jurs P.C. The simulation of carbon-13 nuclear magnetic resonance spectra of dibenzolurans using multiple linear regression analysis and neural networks. Anal. Chim. Acta. 321:1995;127.
11. Ferguson A.M., Heritage T., Jonathan P., Pack S.E., Phillips L., Rogan J., Snaith P.J. EVA-a new theoretically based molecular descriptor for use in QSAR/QSPR analysis. J. Comput. Aided Mol. Design. 11:1997;409-422.
12. Gillie J.K., Hochlowski J., Arbuckte-Keil G.A. Infrared spectroscopy. Anal. Chem. 72:(12):2000;71-79.
13. Hemmer M.C., Steinbauer V., Gasteiger J. The prediction of the 3D structure of organic molecules from their infrared spectra. Vib. Spectrosc. 19:1999;151-164.
14. Herndon W.C., Nowak P.C., Connor D.A., Lin P. Empirical model calculations for thermodynamic and structural properties of condensed polycyclic aromatic hydrocarbons. J. Am. Chem. Soc. 114:1992;41-47.
15. Hosoya H. Topological index: a newly proposed quantity characterizing the topological nature of structural isomers of saturated hydrocarbons. Bull. Chem. Soc. Jpn. 44:1971;2332-2339.
16. Jurs P.C., Ball J.W., Anker L.S., Friedman T.L. Carbon-13 nuclear magnetic resonance spectrum simulation. J. Chem. Inf. Comput. Sci. 32:1992;272.
17. Kier L.B., Hall L.H., Murray W. Molecular connectivity. 1: relationship to nonspecific local anesthesia. J. Pharm. Sci. 64:1975;1971-1974.
18. Kvasnicka V. An application of neural networks in chemistry: prediction of carbon-13 nuclear magnetic resonance shift. J. Math. Chem. 6:1991;63-76.
19. Lavine B.K. Chemometrics. Anal. Chem. 72:(12):2000;91-97.
20. 13C NMR simulation for amino acids. Chin. J. Magn. Reson. 16:(6):1999;553-558. in Chinese.
21. Li Z.L., Zhou L.P., Xia Z.N., Peng H.J., Liu S.S., Yu B.M. On AED-Vector characterization and 13C NMR simulation for sugars. Chin. J. Magn. Reson. 17:(1):2000;55-61. in Chinese.
22. Liu S.S., Li Z.L. Investigation of carbon-13 nuclear magnetic resonance spectra-structure correlation based on novel atomic distance-edge (ADE) vector. Chin. J. Chem. 2:1998;334-339.
23. Liu S.S., Xia Z.N., Yu B.M., Li Z.L. Atomic, electronegative distance vector of acyclic alcohol and chemical shift simulation of 13C NMR spectroscopy. Chin. J. Magn. Reson. 16:(6):1999;429-440. in Chinese.
24. Liu S.S., Xia Z.N., Liu Y., Cai S.X., Li Z.L. An atomic electronegative distance vector arid carbon-13 nuclear magnetic resonance chemical shifts of alcohols and alkanes. Chin. J. Chem. 18:(2):2000;165-174.
25. Liu S.S., Liu H.I., Yu B.M., Cao C.Z., Li Z.L. Investigation on quantitative relationship between chemical shift of carbon-13 nuclear magnetic resonance spectra and molecular lopological structure based on a novel atomic distance-edge vector (ADEV). J. Chemometrics. 15:2001;427-438.
26. Mihalic Z., Vetjan D., Amic D., Nikolic S., Plavsic D., Trinajstic N. The distance matrix in chemistry. J. Math. Chem. 11:1992a;223-258.
27. Mihalic Z., Nikolic S., Trinajstic N. Comparative study of molecular descriptors derived from the distance matrix. J. Chem. Comput. Sci. 32:1992b;28-37.
28. Miyashita Y., Okuyama T., Ohsako H., Sasaki S. Graph theoretical approach to carbon-13 chemical shift sum in alkanes. J. Am. Chem. Soc. 111:1989;3469-3470.
29. Miyashita Y., Li Z.I., Sasaki S. Chemical pattern recognition and multivariate analysis for QSAR studies. Trends Anal. Chem. 12:(2):1993;50-60.
30. O'Sullivan, D.G., Sadler, P.W., 1957. An example of correlation between Taft's sigma* parameters and Infrared spectral frequencies. J. Chem. Soc. 4144-4146.
31. Randie M. On characterization of molecular branching. J. Am. Chem. Soc. 97:1975;6609-6615.
32. Randie M. Generalized molecular descriptors. J. Math. Chem. 7:1991;155-168.
33. Randie M. Novel molecular description for structure-property studies. Chem. Phys. Lett. 211:1993;478-483.
34. Schultz H.P. Topological organic chemistry. I. Graph theory and topological indices of alkanes. J. Chem. Inf. Comput. Sci. 29:1989;227-228.
35. Schultz H.P., Schultz E.B., Schultz T.P. Topological organic chemistry. 9. Graph theory and molecular topological indices of stereoisomeric compounds. J. Chem. Inf. Comput. Sci. 35:1995;864-870.
36. Small G.W., Jurs P.C. Determination of topological similarity of carbon atoms in the simulation of carbon-13 nuclear magnetic resonance spectra. Anal. Chem. 56:1984;2341.
37. Turner D.B., Willell P., Ferguson A.M., Heritage T. Evaluation of a novel infrared range vibration-based descriptor (EVA) for QSAR studies. 1. General application. J. Comput-Aided Mol. Design. 11:1997;409-422.
38. Wiener H. Structure determination of paraffin boiling points. J. Am. Chem. Soc. 69:1947;17-20.