Maleic Anhydride-Furan계와 Maleic Anhydride-Pyrrole계의 Diels-Alder 착체모형에 대한 분자궤도 함수론적 해석(I)

이길준; 김우식; 박병각

Polymer(Korea), Vol.18, No.3, 303-308, May, 1994

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Maleic Anhydride-Furan계와 Maleic Anhydride-Pyrrole계의 Diels-Alder 착체모형에 대한 분자궤도 함수론적 해석(I)

MO Interpretation for Diels-Alder Complex Model of Maleic anhydride-Furan and Maleic Anhydride-Pyrrole Systems(I)

이길준, 김우식, 박병각

초록

Maleic anhydride-Furan계와 Maleic anhydride-Pyrrole계의 교호 공중합의 반응성을 반경험적인 CNDO/2 방법으로 해석하였다. Diels-Alder 형내의 전하이동착체를 가정하여 Maleic anhydride와 Furan사이, Maleic anhydride와 Pyrrole 사이의 전하이동량을 계산하여 각각 2.2518, 2.6381(γ/a.u.)² 값을 얻었다. Maleic anhydride-Pyrrole 착체의 경우 ,Maleic anhydride-Furan 착체보다 안정하므로 공중합이 진행하지 않는다는 것을 추측할 수 있었다. 또한 분자궤도함수론적 관점에서 전하이동착체를 고려하여 poly[(maleic anhydride)-alt-Furan)의 구조에 대해서 논하였다.

The reactivity was interpreted for the alternative copolymerization of Maleic anhydride-Furan and Maleic anhydride-Pyrrole systems by semiempirical CNDO/2 method. The respective values of charge transfer were 2.2518, 2.6381 in the unit of (γ/a.u.)² between Maleic anhydride and Furan, and Maleic anhydride and Pyrrole based on charge transfer complex model of Diels-Alder configuration. Since the charge transfer complex of Maleic anhydride-Pyrrole is considerable stable compared to that of Maleic anhydride-Furan, It would be considered that Maleic anhydride-Pyrrole system does not proceed to alternative copolymerization. We also theoretically discussed the structure of poly[(maleic anhydride)-alt-Furan] on the basis of the above model.

[References]

Mayo FR, Lewis FM, J. Am. Chem. Soc., 66, 1954 (1944)
Ham GE, J. Polym. Sci., 45, 169 (1960)
Dodgson K, Ebdon JR, Eur. Polym. J., 13, 791 (1977)
Odian G, "Principles of Polymerization," 2nd ed., pp. 476-483, Wiley-Interscience Publication, U.S.A. (1981)
Zaitseva VV, Zaitsev SY, Zaitsev YS, Macromolecules, 25, 2551 (1992)
Ebdon JR, Towns CR, Dodgson K, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., C26(4), 523 (1986)
Farmer RG, Hill DJT, O'Donnell JH, J. Macromol. Sci.-Chem., A14(1), 51 (1980)
Butler GB, Do CH, Zerner MC, Macromolecules, 25, 1858 (1992)
Ragab YA, Butler GB, J. Polym. Sci. A: Polym. Chem., 19, 1175 (1981)
Kamo B, Morita I, Horie S, Furusawa S, Polym. J., 6, 121 (1974)
Ragab YA, J. Polym. Sci. A: Polym. Chem., 29, 773 (1991)
Pople JA, Beveridge DL, "Approximate Molecular Orbital Theory," McGraw-Hill, U.S.A. (1970)
Lipkowitz KB, Body DB, "REviews in Computational Chemistry," Vol. 2, p. 489, VCH, U.S.A. (1991)
Butler GB, Bodgett JT, Sharabash M, J. Macromol. Sci.-Chem., A4(1), 51 (1970)
Hall HK, Angew. Chem.-Int. Edit., 22, 440 (1974)

[Referenced By]

[1] Mayo FR, Lewis FM, J. Am. Chem. Soc., 66, 1954 (1944)

[2] Ham GE, J. Polym. Sci., 45, 169 (1960)

[3] Dodgson K, Ebdon JR, Eur. Polym. J., 13, 791 (1977)

[4] Odian G, "Principles of Polymerization," 2nd ed., pp. 476-483, Wiley-Interscience Publication, U.S.A. (1981)

[5] Zaitseva VV, Zaitsev SY, Zaitsev YS, Macromolecules, 25, 2551 (1992)

[6] Ebdon JR, Towns CR, Dodgson K, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., C26(4), 523 (1986)

[7] Farmer RG, Hill DJT, O'Donnell JH, J. Macromol. Sci.-Chem., A14(1), 51 (1980)

[8] Butler GB, Do CH, Zerner MC, Macromolecules, 25, 1858 (1992)

[9] Ragab YA, Butler GB, J. Polym. Sci. A: Polym. Chem., 19, 1175 (1981)

[10] Kamo B, Morita I, Horie S, Furusawa S, Polym. J., 6, 121 (1974)

[11] Ragab YA, J. Polym. Sci. A: Polym. Chem., 29, 773 (1991)

[12] Pople JA, Beveridge DL, "Approximate Molecular Orbital Theory," McGraw-Hill, U.S.A. (1970)

[13] Lipkowitz KB, Body DB, "REviews in Computational Chemistry," Vol. 2, p. 489, VCH, U.S.A. (1991)

[14] Butler GB, Bodgett JT, Sharabash M, J. Macromol. Sci.-Chem., A4(1), 51 (1970)

[15] Hall HK, Angew. Chem.-Int. Edit., 22, 440 (1974)