진동 원편광 이색성 분광기를 사용한 키랄 에폭사이드의 광학순도 분석

이주현; 이충영; 김건중; Joo-Hyun Lee; Choong-Young Lee; Geon-Joong Kim

Applied Chemistry for Engineering, Vol.23, No.6, 577-582, December, 2012

Export Citation

진동 원편광 이색성 분광기를 사용한 키랄 에폭사이드의 광학순도 분석

Determination of Enantiopurity of Chiral Epoxides by Vibrational Circular Dichroism Spectroscopy

이주현, 이충영¹, 김건중 ^†

인하대학교 생명화학공학부
¹인하공업전문대학 화공환경과

Joo-Hyun Lee, Choong-Young Lee¹, and Geon-Joong Kim^†

Department of Chemical Engineering, Inha University, Incheon 402-751, Korea
¹Department of Chemical Environmental Technology, Inha Technical College, Incheon 402-752, Korea

E-mail:

초록

진동 원편광 이색성(VCD; Vibrational Circular Dichroism) 분석기기를 사용한 키랄 유도체의 광학순도 분석을 수행하였다. 이 분석법을 통하여 광학이성체의 절대배위와 2% 이내의 오차 범위 내에서 %EE 값을 용이하게 측정할 수 있었다. 또한 VCD분석을 연속순환방식으로 시간 변화와 함께 수행하여 키랄화합물의 %EE 값을 측정하였다. ECH와 글리시돌 두 키랄 성분이 섞인 2성분 계에서 특별한 분리조작 없이 각 성분에 대한 농도 및 %EE 변화를 동시에 모니터링 하는 것이 가능하였다. 본 연구에서 응용한 VCD 분석법은 반응 중의 반응 속도 등을 연속적으로 측정하는데 유용한 기법이며, 서로 다른 키랄 화합물이 혼합되어 있는 경우에 각각의 광학순도를 시간 변화와 함께 비파괴법으로 측정하기에 편리한 방법임을 확인하였다.

In this work, vibrational circular dichroism (VCD) technique was applied for the determination of %EE of chiral compounds. It may provide an easy way to determine the %EE with a proper accuracy within 2% error ranges as well as the absolute configuration of enantiomers. We demonstrated herein a flow cell VCD (FT-VCD) technique for time-dependent %EE measurements. The simultaneous monitoring of the mole fraction and %EE for two chiral species (epichlorohydrin and glycidol mixture) in the mixture was shown to be successful without any further separation steps. Thus, we demonstrate that FT-VCD is an appropriate analytical tool to monitor the kinetics of reactions involving chiral molecules. FT-VCD also provides a convenient nondestructive approach for the time dependent determination of the optical purity of individual components in a reaction mixture containing chiral molecules.

Keywords:vibrational circular dichroism;absolute configuration;enantiomer;chirality;epichlorohydrin

[References]

Schmid GH, Organic Chemistry, 266, Mosby-Year Book (1996)
Nafie LA, Freedman TB, Enantiomer., 3, 283 (1998)
Dukor RK, Nafie LA, In Encylopedia of Analytical Chemistry; Instrumentation and Applications, eds. Meyers RA, 662, John Wiley and Sons, Chichester, U.K. (2000)
Keiderling TA, In Circular Dichroism, Principles and Applications, 2nd ed., eds.; Berova N, Nakanishi K, Woody R, W., 621,Wiley-VCH, New York (2000)
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Abbate S, Longhi G, Santina C, Chirality., 12, 180 (2000)
Abbate S, Longhi G, Kwon K, Moscowitz A, J. Chem. Phys., 108(1), 50 (1998)
Nafie L, Appl. Spectrosc., 50, A14 (1996)
Nafie LA, Annu. Rev. Phys. Chem., 48, 357 (1997)
Nafie LA, Keiderling TA, Stephens PJ, J. Am. Chem.Soc., 98, 2715 (1976)
Freedman TB, Cao X, Dukor RK, Nafie LA, Chirality., 15, 743 (2003)
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[Related Articles]

[1] Schmid GH, Organic Chemistry, 266, Mosby-Year Book (1996)

[2] Nafie LA, Freedman TB, Enantiomer., 3, 283 (1998)

[3] Dukor RK, Nafie LA, In Encylopedia of Analytical Chemistry; Instrumentation and Applications, eds. Meyers RA, 662, John Wiley and Sons, Chichester, U.K. (2000)

[4] Keiderling TA, In Circular Dichroism, Principles and Applications, 2nd ed., eds.; Berova N, Nakanishi K, Woody R, W., 621,Wiley-VCH, New York (2000)

[5] Berova N, Nakanishi K, Woody RW, Eds. Circular Dichroism: Principlesand Applications, 2nd ed.; Wiley-VCH: New York (2000)

[6] Salvadori P, Ciardelli F, In Optical Rotatory Dispersion and Circular Dichroism; Ciardelli F, Salvadori P, Eds.; Heyden and Sons: Ltd.: London 3 (1973)

[7] Abbate S, Longhi G, Boiadjiev S, Lightner DA, Bertuccic C, Salvadori P, Enantiomer., 3, 337 (1998)

[8] Abbate S, Longhi G, Santina C, Chirality., 12, 180 (2000)

[9] Abbate S, Longhi G, Kwon K, Moscowitz A, J. Chem. Phys., 108(1), 50 (1998)

[10] Nafie L, Appl. Spectrosc., 50, A14 (1996)

[11] Nafie LA, Annu. Rev. Phys. Chem., 48, 357 (1997)

[12] Nafie LA, Keiderling TA, Stephens PJ, J. Am. Chem.Soc., 98, 2715 (1976)

[13] Freedman TB, Cao X, Dukor RK, Nafie LA, Chirality., 15, 743 (2003)

[14] Barron LD, Bogaard MP, Buckingham AD, J. Am.Chem. Soc., 95, 603 (1973)

[15] Hug W, Kint S, Bailey GF, Scherer JR, J. Am. Chem.Soc., 97, 5589 (1975)