Conformational analysis of some trans-4,5-diaryl-1,3-dioxolanes by CD spectroscopy and induction of cholesteric mesophases in nematic solvents: A correlation between twisting power and structure of the dopant

Journal of the American Chemical Society

Volumn 119, Issue 3, 1997, Pages 506-512

  Rosini, Carlo ^a   Spada, Gian Piero ^b   Proni, Gloria ^b   Masiero, Stefano ^b   Scamuzzi, Simone ^c  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0031025810     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962445m     Document Type: Article

References (49)

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19. Michl, J.; Thulstrup, E. W. Spectroscopy with Polarized Light; VCH Publishers: New York, 1986. Sagiv, J. Tetrahedron 1977, 33, 2303.
20. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
21. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
22. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
23. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
24. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
25. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
26. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
27. The term "couplet" has been introduced in 1971 (Haas, G.; Hulbert, P. B.; Klyne, W.; Prelog, V.; Snatzke, G. Helv. Chim. Acta 1971, 54, 491). A couplet (i.e., the presence on the CD spectrum of two bands having equal intensity and opposite sign corresponding to a strong UV absorption) derives from the coupling of allowed transitions, i.e., a coupled oscillator system. The coupled oscillator method for the interpretation of CD spectra goes back to the seminal papers of Kuhn (Trans Faraday Soc. 1930, 26, 293) and Kirkwood (J. Chem. Phys. 1937, 5, 479). This model has been applied to biopolymers by Moffit (J. Chem. Phys. 1956, 25, 467), Tinoco (Adv. Chem. Phys. 1962, 4, 113), and Schellmann et al. (J. Phys. Chem. 1969, 73, 228). The first application in the field of small molecules is due to Mason (Proc. Chem. Soc. 1962, 362) who determined the absolute configuration of the "dimer" alkaloid calycanthine. Applications of this model to structural determinations of natural products can be found in: Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
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