Determination of molecular stereochemistry using optical rotatory dispersion, vibrational circular dichroism and vibrational Raman optical activity

Chiral Analysis

Volumn , Issue , 2006, Pages 461-504

  Polavarapu, Prasad L ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952314501     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044451669-5/50014-4     Document Type: Chapter

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153. A.G. Petrovic, J. He, P.L. Polavarapu, L.S. Xiao and D.W. Armstrong (2005) Absolute configuration and predominant conformations of 1,1-dimethyl-2-phenylethyl phenyl sulfoxide. Org. Biomol. Chem. 3 1977-1981.
154. P.L. Polavarapu (1997) Molecular optical rotations and structures. Tetrahed. Asymmetry 8 3397-3401.
155. P.L. Polavarapu (1997) Abinitio molecular optical rotations and absolute configurations. Mol Phys. 91 551-554.
156. P.L. Polavarapu (2002) Absolute configuration of bromochlorofluoromethane. Angewandte Chem. 41 4544-4546.
157. P.L. Polavarapu (2002) Optical rotation: Recent advances in determining the absolute configuration. Chirality 14 768-781.
158. P.L. Polavarapu (2003) Optical rotation: Recent advances in determining the absolute configuration. Chirality 15 284-285.
159. P.L. Polavarapu (2005) Kramers-Kronig transformation for optical rotatory dispersion studies. J. Phys. Chem. A 109 7013-7023.
160. P.L. Polavarapu and D.K. Chakraborty (1998) Absolute stereochemistry of chiral molecules from ab initio theoretical and experimental molecular optical rotations. J. Am. Chem. Soc. 120 6160-6164.
161. P.L. Polavarapu and D.K. Chakraborty (1999) Ab initio theoretical optical rotations of small molecules. Chem. Phys. 240 1-8.
162. P.L. Polavarapu and C. Zhao (1998) A comparison of ab initio optical rotations obtained with static and dynamic methods. Chem. Phys. Lett. 296 105-110.
163. P.L. Polavarapu and C. Zhao (1999) Ab initio predictions of anomalous optical rotatory dispersion. J. Am. Chem. Soc. 121 246-247.
164. P.L. Polavarapu, D.K. Chakraborty and K. Ruud (2000) Molecular optical rotations: An evaluation of the semiempirical models. Chem. Phys. Lett. 319 595-600.
165. P.L. Polavarapu, A. Petrovic and F. Wang (2003) Intrinsic rotation and molecular structure. Chirality 15 S143-S149.
166. P.L. Polavarapu, A. Petrovic and F. Wang (2003) Intrinsic rotation and molecular structure. Chirality 15 801.
167. P.L. Polavarapu, F. Wang and J. Drabowicz, Determination of absolute configuration of chiral phosphorous compounds from optical rotations (unpublished results).
168. P.L. Polavarapu, J. He, J. Crassous and K. Ruud (2005) Absolute configuration of C76 from optical rtatory dspersion. Chem. Phys. Chem. 6(12), 25.
169. S. Ribe, R.K. Kondru, D.N. Beratan and P. Wipf (2000) Optical rotation computation, total synthesis and stereochemistry assignment of the marine natural product pitimide A. J. Am. Chem. Soc. 122 4608-4617.
170. B.C. Rinderspacher and P.R. Schreiner (2004) Structure-property relationships of prototypical chiral compounds: Case studies. J. Phys. Chem. A 108 2867-2870.
171. K. Ruud and T. Helgaker (2002) Optical rotation studied by density-functional and coupled-cluster methods. Chem. Phys. Lett. 352 533-539.
172. K. Ruud and R. Zanasi (2005) The importance of molecular vibrations: The sign change of the optical rotation of methyloxirane. Angewandte Chem. Int. Ed. 44 3594-3596.
173. K. Ruud, P.R. Taylor and P. Astrand (2001) Zero-point vibrational effects on optical rotation. Chem. Phys. Lett. 337 217-223.
174. K. Ruud, P.J. Stephens, F.J. Devlin, P.R. Taylor, J.R. Cheeseman and M.J. Frisch (2003) Coupled cluster calculations of optical rotation. Chem. Phys. Lett. 373 606-614.
175. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, M.J. Frisch, B. Mennucci and J. Tomasi (2000) Prediction of optical rotation using density functional theory: 6,8-dioxabicyclo[3.2.1]octanes. Tetrahed. Asymmetry 11 2443-2448.
176. P.J. Stephens, F.J. Devlin, J.R. Cheeseman and M.J. Frisch (2001) Calculation of optical rotation using density functional theory. J. Phys. Chem. A 105 5356-5371.
177. P.J. Stephens, F.J. Devlin, J.R. Cheeseman and M.J. Frisch (2002) Ab initio prediction of optical rotation: a comparison of density functional theory and Hartree-Fock methods for three 2,7,8-trioxabicyclo[3.2.1]octanes. Chirality 14 288-296.
178. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, M.J. Frisch and C. Rosini (2002) Determination of absolute configuration using optical rotation calculated using density functional theory. Org. Lett. 4(26), 4595-4598.
179. P.J. Stephens, F.J. Devlin, J.R. Cheeseman, M.J. Frisch, O. Bortolini and P. Beese (2003) Determination of absolute configuration using ab initio calculation of optical rotation. Chirality 15 S57-S64.
180. P.J. Stephens, D.M. McCann, E. Butkus, S. Stoncius, J.R. Cheeseman and M.J. Frisch (2004) Determination of absolute configuration using concerted ab initio DFT calculations of electronic circular dichroism and optical rotation: Bicyclo[3.3.1]nonane diones. J. Org. Chem. 69(6), 1948-1958.
181. P.J. Stephens, D.M. McCann, F.J. Devlin, J.R. Cheeseman and M.J. Frisch (2004) Determination of the absolute configuration of [3(2)](1,4) barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J. Am. Chem. Soc. 126 7514-7521.
182. P.J. Stephens, D.M. McCann, J.R. Cheeseman and M.J. Frisch (2005) Determination of absolute configurations of chiral molecules using ab initio time-dependent density functional theory calculations of optical rotation: How reliable are absolute configurations obtained for molecules with small rotations? Chirality 17 S52-S64.
183. M.C. Tam, N.J. Russ and T.D. Crawford (2004) Coupled cluster calculation of optical rotatory dispersion of (S)-methyloxirane. J. Chem. Phys. 121 3550-3557.
184. S.B. Vogensen, J.R. Greenwood, A.R. Varming, L. Brehm, D.S. Pickering, B. Nielsen, T. Liljefors, R.P. Clausen, T.N. Johansen and P. Krogsgaard-Larsen (2004) A stereochemical anomaly: The cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors. Org. Biomol. Chem. 2 206-213.
185. F. Wang, Y. Wang, P.L. Polavarapu, T. Li, J. Drabowicz, K.M. Pietrusiewicz and K. Zygo (2002) Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphineoxide. J. Org. Chem. 67 6539-6541.
186. F. Wang, P.L. Polavarapu, J. Drabowicz, P. Kielbasinski, M.J. Potrzebowski, M. Mikolajczyk, M.W. Wieczorek, W. Majzner and I. Lazewska (2004) Solution and crystal structures of chiral molecules can be significantly different: Tert-butylphenylphosphinoselenoic acid. J. Phys. Chem. A 108 2072-2079.
187. K.B. Wiberg, P.H. Vaccaro and J.R. Cheeseman (2003) Conformational effects on optical rotation. 3-Substituted 1-butenes. J. Am. Chem. Soc. 125 1888-1896.
188. K.B. Wiberg, Y. Wang, M.J. Murphy and P.K. Vaccaro (2004) Temperature dependence of optical rotation: a-pinene, b-pinene, pinane, camphene, camphor and fenchone. J. Phys. Chem. A 108 5559-5563.
189. K.B. Wiberg, Y. Wang, P.H. Vaccaro, J.R. Cheeseman, G. Trucks and M.J. Frisch (2004) Optical activity of 1-butene, butane and related hydrocarbons. J. Phys. Chem. 108 32-38.
190. G. Zuber, M. Goldsmith, D.N. Beratan and P. Wipf (2005) Assignment of the absolute configuartion of [n]-ladderanes by TD-DFT optical rotation calculations. Chirality 17 507-510.
191. A. Aamouche, F.J. Devlin and P.J. Stephens (2000) 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. 122 7358-7367.
192. A. Aamouche, F.J. Devlin and P.J. Stephens (2000) Structure, vibrational absorption and circular dichroism spectra, and absolute configuration of Troger's base. J. Am. Chem. Soc. 2346-2354.
193. A. Aamouche, F.J. Devlin, P.J. Stephens, J. Drabowicz, B. Bujnicki and M. Mikolajczyk (2000) Vibrational circular dichroism and absolute configuration of chiral sulfoxides: tert-butyl methyl sulfoxide. Chem. Eur. J. 6 4479-4486.
194. V. Andrushchenko, J.L. McCann, J.H. van de Sande and H. Wieser (2000) Determining structures of polymeric molecules by vibrational circular dichroism (VCD) spectroscopy. Vib. Spectrosc. 22 101-109.
195. C.S. Ashvar, F.J. Devlin and P.J. Stephens (1999) Molecular structure in solution: An ab initio vibrational spectroscopy study of phenyloxirane. J. Am. Chem. Soc. 121 2836-2849.
196. D. Bas, T. Burgi, J. Lacour, J. Vachon and J. Weber (2005) Vibrational and electronic circular dichroism of Δ-TRISPHAT [Tris(tetrachlorobenzenediolato)-phosphate(V)] anion. Chirality 17 S143-S148.
197. L.A. Bodack, T.B. Freedman, B.Z. Chowdhry and L.A. Nafie (2004) Solution conformations of cyclosporins and magnesium-cyclosporin complexes determined by vibrational circular dichroism. Biopolymers 73 163-177.
198. P. Bour, K. Zaruba, M. Urbanova, V. Setnicka, P. Matejka, Z. Fiedler, V. Kral and K. Volka (2000) Vibrational circular dichroism of tetraphenylporphyrin in peptide complexes? A computational study. Chirality 12 191-198.
199. P. Bour, H. Navratilova, V. Stnicka, M. Urbanova and K. Volka (2002) (3R, 4S)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine: Conformation and structure monitoring by vibrational circular dichroism. J. Org. Chem. 67 161-168.
200. T. Buffeteau, L. Ducasse, A. Brizard, I. Huc and R. Oda (2004) Density functional theory calculation of vibrational absorption and circular dichroism spectra of dimethyl-L-tartrate. J. Phys. Chem. A. 108 4080-4086.
201. E. Buktus, A. Zilinskas, S. Stoncius, R. Rozenbergas, M. Urbanova, V. Setnicka, P. Bour and K. Volka (2002) Synthesis and chiroptical properties of enantiopure tricyclo[4.4.0.03,8]nonane-4,5-dione (twistbrendanedione). Tetrahed. Asymmetry 13 633-638.
202. T. Burgi, A. Vargaa and A. Baker (2002) VCD spectroscopy of chiral cinchona modifiers used in heterogeneous enantioselective hydrogenation: Conformation and binding of non-chiral acids. J. Chem. Soc. Perkin Trans. 2 1596-1601.
203. C. Cappelli, S. Monti and A. Rizzo (2005) Effect of the environment on vibrational infrared and circular dichroism spectra of (S)-proline. Int. J. Quantum Chem. 104 744-745.
204. R.H. Cichewicz, L.J. Clifford, P.R. Lassen, X. Cao, T.B. Freedman, L.A. Nafie, J.D. Deschamps, V.A. Kenyon, J.R. Flanary, T.R. Holman and P. Crews (2005) Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorg. Med. Chem. 13 5600-5612.
205. F.J. Devlin and P.J. Stephens (1999) Conformational analysis using ab initio vibrational spectroscopy: 3-methylcyclohexanone. J. Am. Chem. Soc. 121 7413-7414.
206. F.J. Devlin, P.J. Stephens, P. Scafato, S. Superchi and C. Rosini (2001) Determination of absolute configuration using vibrational circular dichroism spectroscopy: The chiral sulfoxide 1-thiochroman S-oxide. Tetrahedr. Asymmetry 12 1551-1558.
207. F.J. Devlin, P.J. Stephens, C. Osterle, K.B. Wiberg, J.R. Chesseman and M.J. Frisch (2002) Configurational and conformational analysis of chiral molecules using IR and VCD spectroscopies: spiropentylcarboxylic acid methyl ester and spiropentyl acetate. J. Org. Chem. 67 8090-8096.
208. F.J. Devlin, P.J. Stephens, P. Scafato, S. Superchi and C. Rosini (2002) Conformational analysis using infrared vibrational circular dichroism spectroscopies: the chiral cyclic sulfoxides 1-thiochroman-4-one S-oxide, 1-thiaindan S-oxide and 1-thiochroman S-oxide. J. Phys. Chem. A 106 10510-10524.
209. F.J. Devlin, P.J. Stephens, P. Scafato, S. Superchi and C. Rosini (2002) Determination of absolute configuration using vibrational circular dichroism spectroscopy: the chiral sulfoxide 1-thiochromanone S-oxide. Chirality 14 400-406.
210. F.J. Devlin, P.J. Stephens and P. Besse (2005) Conformational rigidification via derivatization facilitates the determination of absolute configuration using chiroptical spectroscopy: a case study of the chiral alcohol endo-borneol. J. Org. Chem. 70 2980-2993.
211. F.J. Devlin, P.J. Stephens and P. Besse (2005) Are the absolute configurations of 2-(1-hydroxyethyl)-chromen-4-one and its 6-bromo derivative determined by X-ray crystallography correct? A vibrational circular dichroism study of their acetate derivatives. Tetrahedr. Asymmetry 16 1557-1566.
212. J. Dobler, N. Peters, C. Larsson, A. Bergman, E. Geidel and H. Huhnerfuss (2002) The absolute structures of separated PCB-methylsulfone enantiomers determined by vibrational circular dichroisms and quantum mechanical calculations. J. Mol. Struct. (Theochem) 586 159-166.
213. J. Drabowicz, B. Dudzinski, M. Mikolajczyk, F. Wang, A. Dehlavi, J. Goring, M. Park, C. Rizzo, P.L. Polavarapu, P. Biscarini, M.W. Wieczorek and W.R. Majzner (2001) Absolute configuration, predominant conformations and vibrational circular dichroism spectra of enantiomers of n-butyl-t-butyl sulfoxide. J. Org. Chem. 66 1122-1129.
214. D. Dunmire, T.B. Freedman, L.A. Nafie, C. Aeschlimann, J.G. Gerber and J. Gal (2005) Determination of absolute configuration of the antifungal agents ketoconazole, itraconazole, and micoconazole with vibrational circular dichroism. Chirality 17 S101-S108.
215. A.B. Dyatkin, T.B. Freedman, X. Cao, R.K. Dukor, B.E. Maryanoff, C.A. Maryanoff, J.M. Matthews, R.D. Shaw and L.A. Nafie (2002) Determination of the absolute configuration of a key tricyclic component of a novel vasopressin receptor antagonist by use of vibrational circular dichroism. Chirality 14 215-219.
216. T.B. Freedman, X. Cao, D.A. Young and L.A. Nafie (2002) Density functional theory calculations of vibrational circular dichroism in transition metal complexes: Identification of solution conformations and mode of chloride ion association for (+)-tris-(ethylenediaminato)cobalt(III). J. Phys. Chem. A 106 3560-3565.
217. T.B. Freedman, R.K. Dukor, J.C.M. van Hoof, E.R. Kellenbach and L.A. Nafie (2002) Determination of the absolute configuration of (−)-mirtazapine by vibrational circular dichroism. Helv. Chim. Acta 85 1160-1165.
218. T.B. Freedman, X. Cao, R.K. Dukor and L.A. Nafie (2003) Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 15 743-758.
219. T.B. Freedman, X. Cao, L.A. Nafie, M. Kalbermatter, A. Linden and A.J. Rippert (2003) An unexpected atropisomerically stable 1,1-biphenyl at ambient temperature in solution elucidated by vibrational circular dichroism (V.C.D.). Helv. Chim. Acta 86 3141-3155.
220. T.B. Freedman, X. Cao, A. Rajca, H. Wang and L.A. Nafie (2003) Determination of absolute configuration in molecules with chiral axes by vibrational circular dichroism: a C2 symmetric annelated heptathiophene and a D2-symmetric dimer of 1,1′-binaphthyl. J. Phys. Chem. 107 7692-7696.
221. T.B. Freedman, X. Cao, L.A. Nafie, A. Solladie-Cavallo, L. Jierry and L. Bouerat (2004) VCD configuration of enantiopure/-enriched tetrasubstituted a-fluoro cyclohexanones and their use for epoxidation of trans-olefins. Chirality 16 467-474.
222. T.B. Freedman, X. Cao, L.A. Nafie, M. Kalbermatter, A. Linden and A.J. Rippert (2005) Determination of the atropisomeric stability and solution conformation of asymmetrically substituted biphenyls by means of vibrational circular dichroism (VCD). Helvetica Chim. Acta 88 2302-2314.
223. T. Furo, T. Mori, T. Wada and Y. Inoue (2005) Absolute configuration of chiral [2.2]paracylophanes with intramolecular charge-transfer interaction. Failure of the exciton chirality method and use of the sector rule applied to the cotton effect of CT transition. J. Am. Chem. Soc. 127 8242-8243.
224. J. He and P.L. Polavarapu (2005) Determination of inter-molecular hydrogen bonded conformers of a-aryloxypropanoic acids using density functional theory predictions of vibrational absorption and vibrational circular dichroism spectra. J. Chem. Theory Comput. 1 506-514.
225. J. He and P.L. Polavarapu (2005) Determination of the absolute configuration of chiral a-aryloxypropanoic acids using vibrational circular dichroism studies: 2-(2-chlorophenoxy) propanoic acid and 2-(3-chlorophenoxy) propanoic acid. Spectrochim. Acta A 61 1327-1334.
226. J. He, A. Petrovic and P.L. Polavarapu (2004) Quantitative determination of conformer populations: Assessment of specific rotation, vibrational absorption and vibrational circular dichroism. J. Phys. Chem. 108 1671-1680.
227. J. He, F. Wang and P.L. Polavarapu (2005) Absolute configurations of chiral herbicides determined from vibrational circular dichroism. Chirality 17 S1-S8.
228. H. Izumi, S. Futamura, L.A. Nafie and R.K. Dukor (2003) Determination of molecular stereochemistry using vibrational circular dichroism spectroscopy: Absolute configuration and solution conformation of 5-formyl-cis-cis-1,3,5-trimethyl-3-hydroxymethylcyclohexane-1-carboxylic acid lactone. The Chemical Record 3 112-119.
229. T. Kuppens, W. Langenaeker, J.P. Tollenaere and P. Bultinck (2003) Determination of the stereochemistry of 3-hydroxymethyl-2,3-dihydro-[1,4]dioxino[2,3-b]-pyridine by vibrational circular dichroism and the effect of DFT integration grids. J. Phys. Chem. A 107 542-553.
230. K. Monde, T. Taniguchi, N. Miura, S. Njishimura, N. Harada, R.K. Dukor and L.A. Nafie (2003) Preparation of cruciferous phytoalexin related metabolites, (−)-dioxibrassinin and (−)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD). Tetrahedron Lett. 44 6017-6020.
231. T. Mori, H. Izumi and Y. Inoue (2004) Chiroptical properties of organic radical cations. The electronic and vibrational circular dichroism spectra of a-tocopherol derivatives and sterically hindered chiral hydroquinone ethers. J. Phys. Chem. A 108 9540-9549.
232. A. Petrovic, P.L. Polavarapu, J. Drabowicz, Y. Zhang, O.J. McConnell and H. Duddeck (2005) Absolute configuration of C2 symmetric spiroselenurane: 3,3,3′,3′-tetramethyl-1,1′-spirobi[3H,2,1]-benzoxaselenole. Chem. Eur. 11 4257-4262.
233. A. Petrovic, J. He, P.L. Polavarapu, L.S. Xiao and D.W. Armstrong (2005) Absolute configuration and predominant conformations of 1,1-dimethyl-2-phenylethyl phenyl sulphoxide. Org. Biomol. Chem. 3 1977-1981.
234. P.L. Polavarapu and J. He (2004) Chiral analysis using circular dichroism spectroscopy in the mid-infrared. Analytical Chem. 76 61A-67A.
235. P.L. Polavarapu, C. Zhao and K. Ramig (1999) Vibrational circular dichroism, absolute configuration and predominant conformations of volatile anesthetics: 1,2,2,2-tetrafluoroethyl methyl ether. Tetrahedr. Asymmetry 10 1099-1106.
236. P.L. Polavarapu, C. Zhao, A. Cholli and G. Vernice (1999) Vibrational circular dichroism, absolute configuration and predominant conformations of volatile anesthtics: Desflurane. J. Phys. Chem. B 103 6127-6132.
237. G. Roda, P. Conti, M. De Amici, J. He, P.L. Polavarapu and C. De Micheli (2004) Enantiopure stereoisomeric homologues of glutamic acid: Chemoenzymatic synthesis and assignment of their absolute configurations. Tetrahedr. Asymmetry 15 3079-3090.
238. V. Setnicka, M. Urbanova, P. Bour, V. Kral and K. Volka (2001) Vibrational circular dichroism of 1,1′-binaphthyl derivatives: Experimental and theoretical study. J. Phys. Chem. A 105 8931-8938.
239. S.-C. A. Solladie-Cavallo, C. Marsol, G. Pescitelli, L. Di Bari, P. Salvadori, X. Huang, N. Fujioka, N. Berova, X. Cao, T.B. Freedman and L.A. Nafie (2002) (R)-(+)-and (S)-(−)-1-(9-phenanthryl)ethylamine: Assignment of absolute configuration by CD Tweezer and VCD methods, and difficulties encountered with the CD exciton chirality method. Eur. J. Org. Chem. 11 1788-1796.
240. A. Solladie-Cavallo, C. Marsol, M. Yaakoub, K. Azyat, A. Klein, M. Roje, C. Suteu, T.B. Freedman, X. Cao and L.A. Nafie (2003) Erythro-1-naphthyl-1-(2-piperidyl)methanol: Synthesis resolution, NMR relative configuration and VCD absolute configuration. J. Org. Chem. 68 7308-7315.
241. P.J. Stephens and F.J. Devlin (2000) Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 12 172-179.
242. P.J. Stephens, A. Aamouche, F.J. Devlin, S. Superchi, M.I. Donnoli and C. Rosini (2001) Determination of absolute configuration using vibrational circular dichroism spectroscopy: The chiral sulfoxide 1-(2-methynaphthy)methyl sulfoxide). J. Org. Chem. 66 3671-3677.
243. P.J. Stephens, D.M. McCann, F.J. Devlin, T.C. Flood, E. Buktus, S. Stoncius and J.R. Cheeseman (2005) Determination of molecular structure using vibrational ciorcular dichroism spectroscopy: The ketolactone product of Baeyer-Villiger oxidation of (+)-(1R, 5S)-bicyclo[3.31]nonane-2,7-dione. J. Org. Chem. 70 3903-3913.
244. H.Z. Tang, B.M. Novak, J. He and P.L. Polavarapu (2005) A thermal and solvocontrollable cylindrical nanoshutter based on a single screw-sense helical polyguanidine. Angew Chem. Int. Ed. 44 7298-7301.
245. M. Urbanova, V. Setnicka, P. Bour, H. Navratilova and K. Volka (2002) Vibrational circular dichroism spectroscopy study of paroxetine and femoxetine precursors. Biopolymers (Biospectroscopy) 67 298-301.
246. M. Urbanova, V. Setnicka, F. Devlin and P.J. Stephens (2005) Determination of molecular structure in solution using vibrational circular dichroism spectroscopy: The supramolecular teramer of S-2,2′-dimethyl-biphenyl-6,6′-dicarboxylic acid. J. Am. Chem. Soc. 127 6709-6711.
247. C. Vanda, F. Peri, S. Pollicino, A. Ricci, F. Devlin, P.J. Stephens, F. Gasparrini, R. Rompietti and C. Villani (2005) Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and abinition DFT studies of chiral thiepane tetraol derivatives. J. Org. Chem. 70 664-669.
248. F. Wang and P.L. Polavarapu (2000) Vibrational circular dischroism, predominant conformations and hydrogen bonding in (S)-(−)-3-butyn-2-ol. J. Phys. Chem. A 104 1822-1826.
249. F. Wang and P.L. Polavarapu (2000) Conformational stability of (+)-epichlorohydrin. J. Phys. Chem. A 104 6189-6196.
250. F. Wang and P.L. Polavarapu (2000) Vibrational circular dichroism, predominant conformations and intermolecular interaction in (R)-(−)-2-butanol. J. Phys. Chem. A 104 10683-10687.
251. F. Wang and P.L. Polavarapu (2001) Predominant coformations of (2R,3R)-(−)-2,3-butanediol. J. Phys. Chem. A 105 6991-6997.
252. F. Wang, P.L. Povarapu, J. Drabowicz and M. Mikolajczyk (2000) Absolute configurations, predominant conformtaions and tautomeric structures of eantiomeric t-butylphenylphosphine oxides. J. Org. Chem. 65 7561-7565.
253. F. Wang, H. Wang, P.L. Polavarapu and C.J. Rizzo (2001) Absolute configuration and conformational stability of (+)-2,5-dimethylane and (−)-2,5-dimethylsulfolane. J. Org. Chem. 66 3507-3512.
254. F. Wang, P.L. Polavarapu, J. Drabowicz, M. Mikolazczyk and P. Lyzwa (2001) Absolute configurations, predominant conformations and tautomeric structures of enantiomeric tert-butylphenylphosphinothioic acid. J. Org. Chem. 66 9015-9019.
255. F. Wang, P.L. Polavarapu, F. Lebon, G. Longhi, S. Abbate and M. Catellani (2002) Absolute configuration and confomational stability of (S)-(+)-3-(2-methyl butyl)thiophene and (+)-3,4-di[(S)-2-methylbutyl)]thiophene and their polyme. J. Phys. Chem. A 106 5918-5923.
256. F. Wang, P.L. Polavarapu, F. Lebon, G. Longhi, S. Abbate and M. Catellani (2002) Conformational analysis of (S)-(+)-1-bromo-2-methylbutane and the influence of bromine on conformational stability. J. Phys. Chem. 105 12365-12369.
257. F. Wang, P.L. Polavarapu, V. Schurig and R. Schmidt (2002) Absolute configuration and conformational stability of a degradation product of inhalation anesthetic sevoflurane: A vibrational circular dichroism study. Chirality 14 618-624.
258. F. Wang, Y. Wang, P.L. Polavarapu, T. Li, J. Drabowicz, K.M. Pietrusiewicz and K. Zygo (2002) Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphineoxide. J. Org. Chem. 67 6539-6541.
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281. P.L. Polavarapu, T.M. Black, L.D. Barron and L. Hecht (1993) Vibrational Raman optical activity in (R)-(+)-3-methylcyclohexanone: Experimental and ab initio theoretical studies and the origin of unusual couplets. J. Am. Chem. Soc. 115 7736-7742.
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283. P.L. Polavarapu, L. Hecht and L.D. Barron (1993) Vibrational Raman optical activity in substituted oxiranes. J. Phys. Chem. 97 1793-1799.
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290. G. Zuber and W. Hug (2004) Computational interpretation of vibrational optical activity: The ROA spectra of (4S)-4-methylisochromane and the (4S)-isomers of galaxolide. Helv. Chim. Acta 87 2208-2234.
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