Independent Component Analysis Combined with On-line Infrared Spectroscopy for Researching the Synthesis Reaction Mechanism of 3,4-Bis(4'-aminofurazano-3')furoxan†

doi:10.7503/cjcu20130898

Abstract

Abstract:

On-line infrared(IR) spectroscopy was used to monitor the synthesis process of 3,4-bis(4'-ami-nofurazano-3') furoxan(DATF). The IR spectra of components were determined by analyzing the IR data using principal component analysis(PCA) and independent component analysis(ICA). The geometric configurations of intermediates were optimized using the density functional theory(DFT) at B3LYP/6-31+G(d,p) level. Their vibrational frequencies of IR spectra were obtained on the basis of vibrational analysis. The result obtained by the chemometric resolution methods agreed well with that of quantum chemical calculation method, which demonstrated the reliability of the proposed chemometric resolution methods. The unstable intermediate was confirmed via comparing the IR spectra that calculated using B3LYP/6-31+G(d,p) and analyzed by ICA. Finally, the possible synthesis mechanism of DATF was deduced based on the analysis of the above IR spectra. The above mentioned work was expected to provide significant guidance to investigate the reaction mechanism in the future.

Key words: On-line infrared spectrum, Kernel independent component analysis, Density functional theory, Synthesis reaction mechanism, Furoxan

CLC Number:

O657.33

TrendMD:

SUN Kunlun, WU Nan, YANG Huan, YANG Xiaofeng, LI Hua. Independent Component Analysis Combined with On-line Infrared Spectroscopy for Researching the Synthesis Reaction Mechanism of 3,4-Bis(4'-aminofurazano-3')furoxan^†[J]. Chem. J. Chinese Universities, 2014, 35(2): 244.

Figures/Tables 7

Fig.1 IR spectra of 3D image of synthesizing DATF

Table 1 Results of principal component analysis

Principal component number	Eigenvalue of covariance(X)	Variance captured this PC(%)	Variance captured total(%)
1	2.13	99.07	99.07
2	1.38×10^-2	0.64	99.71
3	2.97×10^-3	0.14	99.85
4	1.61×10^-3	0.08	99.93
5	6.37×10^-4	0.03	99.96
6	4.68×10^-4	0.02	99.98

Fig.2 Subspace discrepancy function for number of key variables

Fig.3 IR spectra of reactant(A), intermediate 1(B), intermediate 2(C) and product(D) analyzed by ICA

Fig.4 Geometric configurations of intermediates optimized at B3LYP/ 6-31G* level

Fig.5 Optimized IR spectra of intermediates 1(A) and 2(B)

Scheme 1 Possible reaction mechanism for the synthesis of DATF

References 34

[1]	Sheremeteev A. B., J. Heterocycl. Chem., 1995, 32(2) , 371—385
[2]	Coburn M. D., J. Heterocycl. Chem., 1968, 5(1), 83—87
[3]	Zhou Y. S , Li J. K., Huang X. P ., Propell. Explos. Pyrot., 2007, 30(1), 54—56
	(周彦水, 李建康, 黄新萍.火炸药学报,2007, 30(1), 54—56)
[4]	Zhou Y. S., Wang B. Z., Li J. K., Zhou C., Hu L., Chen Z. Q., Zhang Z. Z., Acta Chimica Sinica, 2011, 69(14), 1673—1680
	(周彦水, 王伯周, 李建康, 周诚, 胡岚, 陈智群, 张志忠.化学学报,2011, 69(14), 1673—1680)
[5]	Luzgin M. V., Kazantsev M. S., Volkova G. G., Wang W., Stepanov A. G., J. Catal., 2011, 277(1), 72—79
[6]	Zhang S. L., Xiong X. F., Wei T., Wang Y. B., Wang B. Z., Ge Z. X., Zhai G. H., Li H., Chem. J. Chinese Universities, 2012, 33(7), 1444—1449
	(张淑利, 熊贤锋, 尉涛, 王友兵, 王伯周, 葛忠学, 翟高红, 李华.高等学校化学学报,2012, 33(7), 1444—1449)
[7]	Li T., Meng Z. H., Wang P., Wang B. Z., Wang K., Ge Z. X., Qin G. M., Li H., Acta Chimica Sinica, 2010, 68(20), 2104—2110
	(李婷, 孟子晖, 王鹏, 王伯周, 王康, 葛忠学, 覃光明, 李华.化学学报,2010, 68(20), 2104—2110)
[8]	Lumpi D., Wagner C., Schopf M., Horkel E., Ramer G., Lendl B., Frohlich J., Chem. Commun., 2012, 48(18), 2451—2453
[9]	Cai L. L., Wang B. Z., Jiao L., Ge Z. X., Qin G. M., Li H., Chin. J. Anal. Chem., 2011, 39(6), 920—924
	(蔡玲玲, 王伯周, 焦龙, 葛忠学, 覃光明, 李华.分析化学,2011, 39(6), 920—924)
[10]	Hyvarinen A., Neural Computing Surveys, 1999, 2(4), 94—128
[11]	Parastar H., Jalali-Heravi M., Tauler R., Trac-trend Anal. Chem., 2012, 31, 134—143
[12]	Herault J., Ans. B., Sciences de la vie., 1984, 299(13), 525
[13]	Cardoso J. F., Laheld B., Signal Processing, 1996, 44(12), 3017—3030
[14]	Bell A. J., Sejnowski T., Neural Comput., 1995, 7(6), 1129—1159
[15]	Hyvrinen A., Oja E., Neural Comput., 1997, 9(7), 1483—1492
[16]	Vigario R. N., Electroencephalogr. Clin. Neurophysiol., 1997, 103(4), 395—404
[17]	Makeig S., Westerfield M., Jung T. P., Enghoff S., Townsend J., Courchesne E., Sejnowski T. J., Science, 2002, 295(5555), 690—694
[18]	Back A. D., Weigend A. S., Int. J. Neural Syst., 1997, 8(4), 473—484
[19]	Visser E., Lee T. W., Chemom. Intell. Lab. Syst., 2004, 70(2), 147—155
[20]	Chuang Y. K., Chen S., Lo Y. M., Tsai C. Y., Yang C., Chen Y. L., Pan P. J., Chen C. C., J. Food Drug Anal., 2012, 20(4), 855—864
[21]	Chen J., Wang X. Z., J. Chem. Inf. Comput. Sci., 2001, 41(4), 992—1001
[22]	Shao X. G., Wang W., Hou Z. Y., Cai W. S., Talanta, 2006, 69(3), 676—680
[23]	Pichler A., Sowa M. G., J. Mol. Spectrosc., 2005, 229(2) , 231—237
[24]	Ren J. Y., Chang C. Q., Fung P. C. W., She J. G. F., Chan H. Y., J. Magn. Reson., 2004, 166(1) , 82—91
[25]	Shao X. G., Wang G. Q., Wang S. F., Su Q. D., Anal. Chem., 2004, 76(17), 5143—5148
[26]	Shao X. G., Liu Z.C., Cai W. S., Analyst, 2009, 134(10), 2095—2099
[27]	Bach F. R., Jordan M. I., J. Mach. Learn. Res., 2002, 3, 1—48
[28]	Wu N., Sun K. L., Liu Y., Yang X. F., Li H., Chem. Res. Chinese Universities, 2013, 29(4), 759—764
[29]	Wang G. Q., Hou Z. Y., Tang Y. X., Zhao T. B., Sun Y. A., Dong C. H., Fu D. X., Anal. Chim. Acta, 2010, 679(1), 43—48
[30]	Zhou Y. S., Wang B. Z., Zhou C., Li J. K., Chen Z. Q., Lian P., Zhang Z. Z., Chinese J. Org. Chem., 2010, 30(7), 1044—1050
	(周彦水, 王伯周, 周诚, 李建康, 陈智群, 廉鹏, 张志忠.有机化学,2010, 30(7), 1044—1050)
[31]	Shen H. L., Liang Y. Z., Kvalheim O. M., Manne R., Chemometr. Intell. Lab., 2000, 51(1), 49—59
[32]	Ali H. R.H., Edwards H. G. M., Kendrick J., Scowe I. J., Spectrochim. Acta A, 2009, 72(2), 244—247
[33]	Frisch M.J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A. Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochter-ski J. W., Ayala P. Y., Mo rokuma K., Voth G. A., Sal-vador P., Dannenberg J. J., Zakrzewski G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Ste-fanov B. B., Liu G., Liashenko A., Piskorz P., Ko-maromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gon-zalez C., Pople J. A., Gaussian 03, Revision D.01,Gaussian Inc.: Wallingford, 2004
[34]	Wong M. W., Chem. Phys. Lett., 1996, 256(4), 391—399