Induced circular dichroism by chiral molecular interaction

Chirality

Volumn 15, Issue 5, 2003, Pages 409-422

  Allenmark, Stig ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

CD spectroscopy; Chiral recognition; Chirality amplification; Inclusion complexes; Induced chirality; Supramolecular chemistry

Indexed keywords

1,2 DIAMINOCYCLOHEXANE; ACETYLENE DERIVATIVE; ALKANE DERIVATIVE; AMPHETAMINE; AZIRINE DERIVATIVE; AZO COMPOUND; BENZOIC ACID DERIVATIVE; BENZOPHENONE; BILIRUBIN; CALIXARENE; CINCHONA ALKALOID; CROWN ETHER; CYCLODEXTRIN; DEOXYCHOLATE SODIUM; ETHANOLAMINE; METALLOPORPHYRIN; PHENOL DERIVATIVE; POLYMER;

ANALYTIC METHOD; AQUEOUS SOLUTION; BINDING SITE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CRYSTAL STRUCTURE; DNA BINDING; GEOMETRY; INTERCALATION COMPLEX; LIGAND BINDING; LIQUID CRYSTAL; MICELLE; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM THEORY; REVIEW; SOLID STATE; ULTRAVIOLET SPECTROSCOPY;

EID: 0038341696     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10220     Document Type: Review

References (117)

1. 2- ion. J Am Chem Soc 1966;88:2606.
2. Hayward LD, Totty RN. Optical activity of symmetric compounds in chiral media. I. Induced circular dichroism of unbound substrates. Can J Chem 1971;49:624-631.
3. Norden B. Solvent-induced circular dichroism. Chem Scr 1975;8:20-22.
4. Otagiri M, Ikeda K, Uekama K, Ito O, Hatano M. Induced circular dichroism of racemic methylcyclohexanones included in β-cyclodextrin. Chem Lett 1974:679-682.
5. Takenaka S, Matsuura N, Tokura N. Induced circular dichroism of benzoylbenzoic acids in β-cyclodextrin. Tetrahedron Lett 1974:2325-2328.
6. Takenaka S, Kondo K, Tokura N. Induced circular dichroism. II. Induced circular dichroism of the 2-benzoylbenzoic acid-amphetamine system in ethereal solvents. J Chem Soc Perkin Trans 2 1974:1749-1752.
7. Takenaka S, Kondo K, Tokura N. Induced circular dichroism. III. Chiroptical properties and ion-pair equilibria in 2-benzoylbenzoic acid-amphetamine. J Chem Soc Perkin Trans 2 1975:1520-1524.
8. Rosenfeld L. Quantenmechanische Theorie der natürlichen optischen Aktivität von Flüssigkeiten und Gasen. Z Phys 1928;52:161-174.
9. Schellman JA. Symmetry rules for optical rotation. Acc Chem Res 1968;1:144-151.
10. Tinoco I Jr. Theoretical aspects of optical activity. II. Polymers. Adv Chem Phys 1962;4:113-160.
11. Harada N, Nakanishi K. Circular dichroic spectroscopy; exciton coupling in organic stereochemistry. Mill Valley, CA: University Science Books; 1983.
12. Inskeep WH, Miles DW, Eyring H. Circular dichroism of nucleoside derivatives. 8. Coupled oscillator calculations of molecules with fixed structure. J Am Chem Soc 1970;92:3866-3872.
13. Ardhammar M, Nordén B, Kurucsev T. DNA-Drug interactions. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 741-768.
14. Craig DP, Power EA, Thirunamachandran T. Induced circular dichroism. Theoretical description. Chem Phys Lett 1974;27:149-153.
15. Mason SF. Induced circular dichroism. Chem Phys Lett 1975;32:201-203.
16. Snatzke G. Chiroptical methods in stereochemistry. I. Chem Unserer Zeit 1981;15:78-87.
17. Snatzke G. Chiroptical methods in stereochemistry. II. Chem Unserer Zeit 1982;16:160-168.
18. Snatzke G, Woody RW. Circular dichroism: an introduction. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 1-35.
19. Rodger A, Nordén B. Circular dichroism and linear dichroism. Oxford: Oxford University Press; 1997.
20. Sandström J. Determination of absolute configurations and conformations by semiempirical calculation of CD spectra. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 459-490.
21. 1-acid glycoprotein. Biochem Pharmacol 1991;42:729-733.
22. Nezu T, Ikeda S. Induced circular dichroism of a cationic porphyrin bound to α-helical poly(L-glutamic acid) and β-form poly[S-(carboxymethyl)-L-cysteine] in aqueous solutions. Bull Chem Soc Jpn 1993;66:18-24.
23. Brittain HG. Applications of chiroptical spectroscopy in the characterization of compounds having pharmaceutical importance. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 819-844.
24. Perrin JH, Wilsey M. The induced optical activity of bilirubin in the presence of sodium deoxycholate. Chem Commun 1971:769-770.
25. Gawronski J, Gawronska K. Induced circular dichroism of the sulfonephthalein-cinchona alkaloid system: a correlation with cinchona alkaloid-catalyzed asymmetric addition reactions. J Chem Res Synop 1984:304-305.
26. Lightner DA, Gawronski JK, Wijekoon WMD. Complementarity and chiral recognition: enantioselective complexation of bilirubin. J Am Chem Soc 1987;109:6354-6362.
27. Shimizu H, Kaito A, Hatano M. Induced circular dichroism of β-cyclodextrin complexes with substituted benzenes. Bull Chem Soc Jpn 1979;52:2678-2684.
28. Shimizu H, Kaito A, Hatano M. Induced circular dichroism of β-cyclodextrin complexes with o-, m-, and p-disubstituted benzenes. Bull Chem Soc Jpn 1981;54:513-519.
29. Shimizu H, Kaito A, Hatano M. Induced circular dichroism of β-cyclodextrin complexes with azanaphthalenes - polarization directions of the π* ← π transitions in azanaphthalenes. J Am Chem Soc 1982;104:7059-7065.
30. Harata K, Uedaira H. Circular dichroism spectra of the β-cyclodextrin complex with naphthalene derivatives. Bull Chem Soc Jpn 1975;48: 375-378.
31. Harata K. Induced circular dichroism of cycloamylose complexes with meta- and para-disubstituted benzenes. Bioorg Chem 1981;10:255-265.
32. Kodaka M. Sign of circular dichroism induced by β-cyclodextrin. J Phys Chem 1991;95:2110-2112.
33. Kodaka M. A general rule for circular dichroism induced by a chiral macrocycle. J Am Chem Soc 1993;115:3702-3705.
34. Matsuura N, Takenaka S, Tokura N. Formation of inclusion complexes of benzophenone derivatives; β-cyclodextrin studied by induced circular dichroism. J Chem Soc Perkin Trans 2 1977:1419-1421.
35. Kobayashi N, Saito R, Hino H, Hino Y, Ueno A, Osa T. Fluorescence and induced circular dichroism studies on host-guest complexation between γ-cyclodextrin and pyrene. J Chem Soc Perkin Trans 2 1983:1031-1035.
36. Kobayashi N, Hino Y, Ueno A, Osa T. Induced circular dichroism of two chromophores included in γ-cyclodextrin. Bull Chem Soc Jpn 1983;56:1849-1850.
37. Kobayashi N, Osa T. Inclusion of ferrocenecarboxylic acid and its carboxylate anion by β-cyclodextrin as observed by induced circular dichroism. Chem Lett 1986:421-424.
38. Kodaka M, Fukaya T. Induced circular dichroism spectrum of a α-cyclodextrin complex with heptylviologen. Bull Chem Soc Jpn 1989;62: 1154-1157.
39. Patonay G, Warner IM. Investigation of induced circular dichroism of benzo(a)pyrene cyclodextrin complexes. J Inclus Phenom Mol Recog Chem 1991;11:313-322.
40. Boisvin M, Rassat A, Le Bas G, Tsoucaris G. Internal and external induced circular dichroism in cyclodextrin complexes: a study of the complexes of α-cyclodextrin with (R)-3-methylcyclopentanone and cyclopentanone. Croat Chem Acta 1989;62:401-410.
41. Aoyagi M, Kubozono Y, Ata M, Gondo Y. Induced circular dichroism spectrum of 4,4′-bipyridyl radical cation-β-cyclodextrin inclusion complex. Chem Phys Lett 1986;131:201-204.
42. Buvari-Barcza A, Kajtar J, Szente L, Barcza L. Hydroxypropyl-β-cyclodextrins: induced circular dichroism spectra of included phenolphthalein as a function of the degree of substitution. J Chem Soc Perkin Trans 2 1996:489-491.
43. Fornasier R, Resente C, Tonellato U. Binding modes of azulene with β-cyclodextrins of different lipophilic character: an induced circular dichroism study. Gazz Chim Ital 1992;122:169-170.
44. Yoshida N, Yamaguchi H, Higashi M. Induced circular dichroism spectra of α-, β-, and γ-cyclodextrin complexes with sodium 4′-hydroxy-3′-isopropylazobenzene-4-sulfonate and sodium 4′-hydroxy-3′,5′-diisopropylazobenzene-4-sulfonate. J Chem Soc Perkin Trans 2 1994:2507-2513.
45. Yoshida N, Yamaguchi H, Iwao T, Higashi M. Induced circular dichroism spectra of α-, β-, and γ-cyclodextrin complexes with π-conjugate compounds. 2. Chiral dimer formation and polarization directions of the π → π* transitions in some hydroxyazo guests having a naphthalene nucleus. J Chem Soc Perkin Trans 2 1999:379-386.
46. Lightner DA, Gawronski JK, Gawronska K. Conformational enantiomerism in bilirubin. Selection by cyclodextrins. J Am Chem Soc 1985;107:2456-2461.
47. Zhdanov YA, Alekseev, Yu E, Kompantseva E, Vergeichik EN. Induced optical activity in cyclodextrin complexes. Russ Chem Rev 1992;61:1025-1042.
48. Klein H. Induzierter Circulardichroismus in Kronenethern durch Complexierung mit optisch aktiven Ammoniumsalzen. Tetrahedron Lett 1979:3835-3838.
49. Kaneko O, Matsuura N, Kimura K, Shono T. Induced circular dichroism of substituted benzophenones by complexation with chiral crown ethers. Chem Lett 1979:369-372.
50. Lazar A, Angyan JG, Hollosi M, Huszthy P, Surjan PR. Theoretical CD spectrum calculations of the crown-ether aralkyl-ammonium salt complex. Chirality 2002;14:377-385.
51. Gutsche CD. Calixarenes. Acc Chem Res 1983;16:161-170.
52. Shinkai S, Arimura T, Satoh H, Manabe O. Chiral calixarene. J Chem Soc Chem Commun 1987:1495-1496.
53. Arimura T, Kawabata H, Matsuda T, Muramatsu T, Satoh H, Fujio K, Manabe O, Shinkai S. New water-soluble host calixarenes bearing chiral substituents. J Org Chem 1991;56:301-306.
54. Morozumi T, Shinkai S. A novel "reading-out" system for amino acid chirality with induced chirality in water-soluble calix[n]arenes. Chem Lett 1994:1515-1518.
55. Morozumi T, Shinkai S. Induced circular dichroism detection of chiral ammonium guests through inclusion in calix[n]arene cavities. J Chem Soc Chem Commun 1994:1219-1220.
56. Kikuchi Y, Kobayashi K, Aoyama Y. Molecular recognition. 18. Complexation of chiral glycols, steroidal polyols, and sugars with a multibenzenoid, achiral host as studied by induced circular dichroism spectroscopy: exciton chirality induction in resorcinol-aldehyde cyclotetramer and its use as a supramolecular probe for the assignments of stereochemistry of chiral guests. J Am Chem Soc 1992;114:1351-1358.
57. Arimura T, Edamitsu S, Shinkai S, Manabe O, Muramatsu T, Tashiro M. Induced circular dichroism in calixarene complexes. Chem Lett 1987:2269-2272.
58. Arimura T, Shinkai S. Formation of molecular complexes with calixarenes as detected by induced circular dichroism. Bull Chem Soc Jpn 1991;64:1896-1900.
59. Arimura T, Shibata M, Ihara H, Hirayama C. Evaluation of selective binding ability in chiral supramolecules using induced chirality. Anal Sci 1993;9:401-403.
60. Mizutani T, Takagi H, Hara O, Horiguchi T, Ogoshi H. Axial chirality induction in flexible biphenols by hydrogen bonding and steric interactions. Tetrahedron Lett 1997;38:1991-1994.
61. Hosoi S, Kamiya M, Ohta T. Novel development of exciton-coupled circular dichroism based on induced axial chirality. Org Lett 2001;3:3659-3662.
62. Takenaka S, Sugiyama M, Tokura N. Ion-pair aggregation of a longchain carboxylic acid and an amine in benzene studied by induced circular dichroism. J Chem Soc Perkin Trans 2 1976:555-559.
63. Gawronski J. Micelle-induced circular dichroism of aliphatic ketones. Tetrahedron Lett 1976:3845-3846.
64. Tachibana T, Kurihara K. Induced circular dichroism of achiral dye solubilizates in aqueous micellar solutions of a chiral surfactant. Naturwiss 1976;63:532-533.
65. Nakagawa H, Kobori Y, Yamada K-I. Spontaneous chirality conversion of [5]thiaheterohelicene in charge tranfer complexes in SDS micelles. Chirality 2001;13:722-726.
66. Saeva FD, Wysocki JJ. Induced circular dichroism in cholesteric liquid crystals. J Am Chem Soc 1971;93:5928-5929.
67. Saeva FD. Cholesteric liquid-crystal-induced circular dichroism (LCICD) of achiral solutes. Novel spectroscopic technique. J Am Chem Soc 1972;94:5135-5136.
68. Saeva FD, Olin GR. Cholesteric liquid crystal induced circular dichroism (LCICD). VII. LCICD of achiral solutes in lyotropic cholesteric mesophases. J Am Chem Soc 1973;95:7882-7884.
69. Saeva FD, Sharpe PE, Olin GR. Cholesteric liquid crystal induced circular dichroism (LCICD). VI. LCICD behavior of benzene and some of its mono- and disubstituted derivatives. J Am Chem Soc 1973;95:7660-7663.
70. Borovkov VV, Yamamoto N, Lintuluoto JM, Tanaka T, Inoue Y. Supramolecular chirality induction in bis(zinc porphyrin) by amino acid derivatives: rationalization and applications of the ligand bulkiness effect. Chirality 2001;13:329-335.
71. Liu H-Y, Huang J-W, Tian X, Jiao X-D, Luo G-T, Ji L-N. The synthesis and spectroscopic characterization of a chiral zinc(II) porphyrin dimer containing an amino acid bridge: model complexes for the induced circular dichroism of porphyrin protein supramolecules. Inorg Chim Acta 1998;272:295-299.
72. Miyoshi K, Oh CE, Nakazawa H, Yoneda H. Induced circular dichroism spectra of some achiral and racemic cobalt(III)-amine complexes in aqueous (R,R)-tartrate and (R,R)-tartratoantimonate(III) solutions. Bull Chem Soc Jpn 1978;51:2946-2950.
73. Nakazawa H, Oh CE, Miyoshi K, Yoneda H. Induced circular dichroism spectra of some racemic cis-bis(ethylenediamine)cobalt(III) complexes in aqueous (R,R)-tartrate and (R,R)-tartratoantimonate(III) solutions and their optical resolution by ion-exchange chromatography. Bull Chem Soc Jpn 1980;53:273-274.
74. Murakami T. Induced circular dichroism of bis(tropolonato)copper(II) with optically active amines. Bull Chem Soc Jpn 1985;58:3411-3412.
75. Tamiaki H, Matsumoto N, Unno S, Shinoda S, Tsukube H. Induced circular dichroism active complexes of synthetic gadolinium(III) porphyrinates with chiral amino acids. Inorg Chim Acta 2000;300-302:243-249.
76. Tanaka K, Kato M, Toda F. Induced circular dichroism in solid-state inclusion compounds. Chirality 2001;13:347-350.
77. Ogoshi H, Mizutani T. Multifunctional and chiral porphyrins: model receptors for chiral recognition. Acc Chem Res 1998;31:81-89.
78. Yashima E, Matsushima T, Okamoto Y. Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexation. J Am Chem Soc 1997;119:6345-6359.
79. Pirkle WH, Rinaldi PL. Use of liquid-crystal-induced circular dichroism for determination of absolute configuration of alcohols and oxaziridines. J Org Chem 1980;45:1379-1382.
80. Rinaldi PL, Naidu MSR, Conaway WE. Absolute configuration determinations of chiral α-substituted benzylamines using liquid crystalinduced circular dichroism. J Org Chem 1982;47:3987-3991.
81. Rinaldi PL, Wilk M. Use of liquid crystal induced circular dichroism for absolute configurational assignments of β-amino alcohols. J Org Chem 1983;48:2141-2146.
82. Saeva FD. Relation between cholesteric and nematic mesophases. Mol Cryst Liquid Cryst 1973;23:171-177.
83. Gottarelli G, Samori B, Marzocchi S, Stremmenos C. Induction of a cholesteric mesophase in a nematic liquid crystal by some optically active alcohols. Possible method for the correlation of configurations. Tetrahedron Lett 1975:1981-1984.
84. Gottarelli G, Samori B, Folli U, Torre G. Induction of cholesteric mesophases in nematic liquid crystals by some optically active sulfoxides: relationship between the absolute configurations, the dimensions of the substituents and the handness of the induced mesophases. J Phys Colloq (Orsay, Fr) 1979:25-26.
85. Gottarelli G, Spada GP, Solladie G. Some stereochemical applications of induced cholesteric liquid crystals. Nouv J Chim 1986;10:691-696.
86. Yashima E, Okamoto Y. Induced CD of polymers. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 521-546.
87. Mizutani T, Ema T, Yoshida T, Kuroda Y, Ogoshi H. Recognition of α-amino acid esters by zinc porphyrin derivatives via coordination and hydrogen bonding interactions. Evidence for two-point fixation from thermodynamic and induced circular dichroism spectroscopic studies. Inorg Chem 1993;32:2072-2077.
88. Mizutani T, Ema T, Yoshida T, Renne T, Ogoshi H. Mechanism of induced circular dichroism of amino acid ester-porphyrin supramolecular systems. Implications to the origin of the circular dichroism of hemoprotein. Inorg Chem 1994;33:3558-3566.
89. Mizutani T, Kurahashi T, Murakami T, Matsumi N, Ogoshi H. Molecular recognition of carbohydrates by zinc porphyrins: Lewis acid/ Lewis base combinations as a dominant factor for their selectivity. J Am Chem Soc 1997;119:8991-9001.
90. Huang X, Nakanishi K, Berova N. Porphyrins and metalloporphyrins: versatile circular dichroic reporter groups for structural studies. Chirality 2000;12:237-255.
91. Huang X, Borhan B, Rickman BH, Nakanishi K, Berova N. Zinc porphyrin tweezer in host-guest complexation: determination of absolute configurations of primary monoamines by circular dichroism. Chem-Eur J 2000;6:216-224.
92. Kurtan T, Nesnas N, Li Y-Q, Huang X, Nakanishi K, Berova N. Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 1. Chiroptical protocol for absolute configurational assignments of monoalcohols and primary monoamines. J Am Chem Soc 2001;123:5962-5973.
93. Kurtan T, Nesnas N, Koehn FE, Li Y-Q, Nakanishi K, Berova N. Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 2. Structural studies of host-guest complexes with chiral alcohol and monoamine conjugates. J Am Chem Soc 2001;123:5974-5982.
94. Hosoi S, Kamiya M, Fumiyuki K, Ohta T. Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols. Tetrahedron Lett 2001;42:6315-6317.
95. Tsukube H, Hosokubo M, Wada M, Shinoda S, Tamiaki H. Chirality probing of amino alcohols with lanthanide complexes via induced circular dichroism spectroscopy. J Chem Soc Dalton Trans 1999:11-12.
96. Ata M, Yamaguchi H. Molecular orientation of naphthalene-1,4-diol in a β-cyclodextrin inclusion complex. Chem Commun 1983:3-4.
97. Ata M, Kubozono Y, Suzuki Y, Aoyagi M, Gondo Y. Induced circular dichroism and molecular orientations of β-cyclodextrin inclusion complexes with 9,10-anthraquinone and 9,10-phenanthrenequinone. Bull Chem Soc Jpn 1989;62:3706-3708.
98. Yamaguchi H, Ikeda N, Uekama K, Hirayama F. Analysis of the vibrational structure in induced circular dichroism of chlorobenzene included in β-cyclodextrin. Z Phys Chem 1978;109:173-178.
99. Yamaguchi H, Uchida A, Yoneda F, Baumann H. Magnetic circular dichroism spectra and electronic spectra of benzodiazoles. J Chem Soc Faraday Trans 2 1981;77:947-954.
100. Yamaguchi H, Abe S. Vibrational structures in circular dichroism of monosubstituted benzenes included in β-cyclodextrin. J Phys Chem 1981;85:1640-1643.
101. Yamaguchi H, Fukuda M, Takeshita H, Mametsuka H, Baumann H. Electronic spectra of 1,3-diazaazulene. J Chem Soc Faraday Trans 2 1982;78:193-199.
102. Yamaguchi H. Induced circular dichroism spectra of cyclobuta[1,2-b: 3,4-b′]diquinoxaline. J Inclus Phenom 1984;2:747-753.
103. Yamaguchi H, Higashi M. Induced circular dichroism spectra of benz[b]anthracene included in &-cyclodextrin. J Inclus Phenom 1987; 5:725-728.
104. Yamaguchi H, Higashi M, Nakayama J, Hoshino M. Induced circular dichroism spectra of the cyclodextrin complexes with 2-thioxo-1,3-benzodithiole and 2-selenoxo-1,3-benzodithiole. J Inclus Phenom Mol Recog Chem 1990;9:253-257.
105. Zhang X, Nau WM. Chromophore alignment in a chiral host provides a sensitive test for the orientation-intensity rule of induced circular dichroism. Angew Chem Int Ed 2000;39:544-547.
106. Mayer B, Zhang X, Nau WM, Marconi G. Co-conformational variability of cyclodextrin complexes studied by induced circular dichroism of azoalkanes. J Am Chem Soc 2001;123:5240-5248.
107. Krois D, Brinker UH. Induced circular dichroism and UV-Vis absorption spectroscopy of cyclodextrin inclusion complexes: structural elucidation of supramolecular azi-adamantane (spiro[adamantane-2,3′-diazirine]). J Am Chem Soc 1998;120:11627-11632.
108. Bobek MM, Krois D, Brinker UH. Induced circular dichroism of cyclodextrin inclusion complexes: examining the cavity with a bilateral probe. Org Lett 2000;2:1999-2002.
109. Green MM, Lifson S, Teramoto A. Cooperation in a deep helical energy well. Chirality 1991;3:285-291.
110. Khatri CA, Andreola C, Peterson NC, Green MM. Chiral solvation enforced helix sense excess in poly(n-hexyl isocyanate) (PHIC) dissolved in (R)-2-chlorobutane. Polym Prepr (Am Chem Soc, Div Polym Chem) 1992;33:200-201.
111. Green MM, Park J-W, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV. The macromolecular route to chiral amplification. Angew Chem Int Ed 1999;38:3139-3154.
112. Green MM. A model for how polymers amplify chirality. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 491-520.
113. Jackson K, Mason SF. Linear and circular dichroism studies of DNA-monoaminoacridine complexes. Trans Faraday Soc 1971;67:966-989.
114. Fornasiero D, Kurucsev T. Circular dichroism spectra and the interaction between acridine dyes and deoxyribonucleic acid. J Phys Chem 1981;85:613-618.
115. Owen D, Schuster GB. Induced circular dichroism in cyanine borate penetrated ion pairs. J Am Chem Soc 1996;118:259-260.
116. Owen DJ, VanDerveer D, Schuster GB. Cyanine borate penetrated ion pair structures in solution and the solid state: induced circular dichroism. J Am Chem Soc 1998;120:1705-1717.
117. Eliel EL, Wilen SH, Mander LN, Stereochemistry of organic compounds. New York: Wiley; 1994.