Unusual CD couplet pattern observed for the π* ← n transition of enantiopure (Z)-8-methoxy-4-cyclooctenone: An experimental and theoretical study by electronic and vibrational circular dichroism spectroscopy and density functional theory calculation

Chirality

Volumn 19, Issue 5, 2007, Pages 415-427

  Tanaka, Takeyuki ^a   Oelgemöller, Michael ^b   Fukui, Keijiro ^c   Aoki, Fumiko ^c   Mori, Tadashi ^c   Ohno, Takashi ^a   Inoue, Yoshihisa ^c,d  

^a KOBE UNIVERSITY   (Japan)

^b DUBLIN CITY UNIVERSITY   (Ireland)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d OSAKA UNIVERSITY   (Japan)

Author keywords

Band resolution; Conformation; Cotton effect; ECD; TD DFT; VCD

Indexed keywords

8 METHOXY 4 CYCLOOCTENONE; CYCLOOCTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; ENERGY; LIGHT ABSORPTION; PRIORITY JOURNAL; SPECTRAL SENSITIVITY; TEMPERATURE; ULTRAVIOLET SPECTROSCOPY;

EID: 34247569359     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20391     Document Type: Article

References (38)

1. Inoue Y, Yokoyama T, Yamasaki N, Tai A. Temperature switching of product chirality upon photosensitized enantiodifferentiating cis-trans isomerization of cyclooctene. J Am Chem Soc 1989;111:6480-6482.
2. Inoue Y, Yamasaki N, Yokoyama T, Tai A. Enantiodifferentiating Z-E photoisomerization of cyclooctene sensitized by chiral polyalkyl benzenepolycarboxylates. J Org Chem 1992;57:1332-1345.
3. Inoue Y, Yamasaki N, Yokoyama T, Tai A. Highly enantiodifferentiating photoisomerization of cyclooctene by congested and/or triplex-forming chiral sensitizers. J Org Chem 1993;58:1011-1018.
4. Inoue Y, Tsuneishi H, Hakushi T, Tai A. Optically active (E,Z)-1,3-cyclooctadiene: first enantioselective synthesis through asymmetric photosensitization and chiroptical property. J Am Chem Soc 1997;119:472-478.
5. Inoue Y, Matsushima E, Wada T. Pressure and temperature control of product chirality in asymmetric photochemistry: enantiodifferentiating photoisomerization of cyclooctene sensitized by chiral benzenepoly-carboxylates. J Am Chem Soc 1998;120:10687-10696.
6. Inoue Y, Ueoka T, Kuroda T, Hakushi T. Singlet photosensitization of simple alkenes, Part 4: cis-trans photoisomerization of cycloheptene sensitized by aromatic esters: Some aspects of the chemistry of trans- cycloheptene. J Chem Soc Perkin Trans 2 1983;7:983-988.
7. Fukui K, Naitoh Y, Taniguchi S, Inoue Y. 4-Cyclooctenone: chiroptical properties and absolute asymmetric synthesis. Book of abstracts: First International Symposium on Asymmetric Photochemistry, Osaka, Japan, 2001.
8. Inoue Y. Asymmetric photochemical reactions in solution. Chem Rev 1992;92:741-770.
9. Oelgemöller M, Fukui K, Tanaka T, Inoue Y. Synthesis, photochemistry and photophysical properties of cyclooctene and cyclooctenone. Book of abstracts: First International Symposium on Asymmetric Photochemistry, Osaka, Japan, 2001.
10. Barron LD. Molecular light scattering and optical activity. Cambridge: Cambridge University Press; 2004. p 443.
11. Nafie LA. Infrared and Raman vibrational optical activity: theoretical and experimental aspects. Annu Rev Phys Chem 1997;48:357-386.
12. Stephens PJ, Lowe MA. Vibrational circular dichroism. Annu Rev Phys Chem 1985;36:213-241.
13. Holzwarth G, Chabay I. Optical activity of vibrational transitions: a coupled oscillator model. J Chem Phys 1972;57:1632-1635.
14. Hohn EG, Weigang OE Jr. Electron correlation models for optical activity. J Chem Phys 1968;48:1127-1137.
15. Weigang OE Jr. An amplified sector rule for electric dipole-allowed transitions. J Am Chem Soc 1979;101:1965-1975.
16. Tanaka T, Inoue K, Kodama T, Kyogoku Y, Hayakawa T, Sugeta H. Conformational study on polyγ-(α-phenethyl)-l-glutamate using vibrational circular dichroism spectroscopy. Biopolymers 2001;62:228-234.
17. Wilson EB, Decius JC, Cross PC. Molecular vibrations: the theory of infrared and Raman vibrational spectra. New York: McGraw-Hill; 1955. p 388.
18. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ. Ab Initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996;252:211-220.
19. Bak KL, Jorgensen P, Helgaker T, Ruud K, Jensen HJA. Gauge-origin independent multiconfigurational self-consistent-field theory for vibrational circular dichroism. J Chem Phys 1993;98:8873-8887.
20. Monde K, Taniguchi T, Miura N, Vairappan CS, Suzuki M. Absolute configurations of endoperoxides determined by vibrational circular dichroism (VCD). Tetrahedron Lett 2006;47:4389-4392.
21. Devlin FJ, Stephens PJ, Scafato P, Superchi S, Rosini C. Determination of absolute configuration using vibrational circular dichroism spectroscopy: the chiral sulfoxide 1-thiochroman S-oxide. Tetrahedron Asymmetry 2001;12:1551-1558.
22. Solladié-Cavallo A, Balaz M, Salisova M, Suteu C, Nafie LA, Cao X, Freedman TB. A new chiral oxathiane: synthesis, resolution and absolute configuration determination by vibrational circular dichroism. Tetrahedron Asymmetry 2001;12:2605-2611.
23. Aamouche A, Devlin FJ, Stephens PJ. Conformations of chiral molecules in solution: ab initio vibrational absorption and circular dichroism studies of 4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone and 3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione. J Am Chem Soc 2000;122:7358-7367.
24. Zhao C, Polavarapu PL, Grosenick H, Schurig V. Vibrational circular dichroism, absolute configuration and predominant conformations of volatile anesthetics: Enflurane. J Mol Struct 2000;550/551:105-115.
25. Ashvar CS, Devlin FJ, Stephens PJ. Molecular structure in solution: an ab Initio vibrational spectroscopy study of phenyloxirane. J Am Chem Soc 1999;121:2836-2849.
26. Wiberg KB, Stratmann RE, Frisch MJ. A time-dependent density functional theory study of the electronically excited states of formaldehyde, acetaldehyde and acetone. Chem Phys Lett 1998;297:60-64.
27. Guan J, Casida ME, Salahub DR. Time-dependent density-functional theory investigation of excitation spectra of open-shell molecules. J Mol Struct 2000;527:229-244.
28. Petiau M, Fabian J. The thiocarbonyl chromophore: A time-dependent density-functional study. J Mol Struct 2001;538:253-260.
29. Gross EKU, Kohn W. Density functional theory of many-Fermion systems, SB Trickey Ed. Adv Quantum Chem 1990;21:255-291.
30. Diedrich C, Grimme S. Systematic investigation of modern quantum chemical methods to predict electronic circular dichroism spectra. J Phys Chem A 2003;107:2524-2539.
31. Furche F, Ahlrichs R, Wachsmann C, Weber E, Sobanski A, Vögtle F, Grimme S. Circular dichroism of helicenes investigated by time-dependent density functional theory. J Am Chem Soc 2000;122:1717-1724.
32. Oelgemöller M, Fukui K, Hesek D, Aoki F, Niki M, Inoue Y. The formation of spiro-bridged dimers of cyclooctane-1,2-dicarbonyl compounds via domino aldol-cycloalkylation. Heterocycles 2002;57:741-747.
33. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B 05. Pittsburgh, PA Gaussian Inc.; 2003.
34. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98:5648-5652.
35. McLean AD, Chandler GS. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z = 11 - 18. J Chem Phys 1980;72:5639-5648.
36. Krishnan R, Binkley JS, Seeger R, Pople JA. Self-consistent orbital methods. XX. A basis set for correlated wave functions. J Chem Phys 1980;72:650-654.
37. Foresman JB, Frisch Æ. Exploring chemistry with electronic structure methods: a guide to using Gaussian. Pittsburgh: Gaussian Inc.; 1993; p 302.
38. Dierksen M, Grimme S. The vibronic structure of electronic absorption spectra of large molecules: a time-dependent density functional study on the influence of "exact" Hartree-Fock exchange. J Phys Chem A 2004;108:10225-10237.