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LITERATURE CITED

  • 1
    Rosenfeld L. Quantum-mechanical theory of the natural optical activity of liquids and gases. Z Phys 1928; 52: 161174.
  • 2
    Condon EU. Theories of optical rotatory power. Rev Mod Phys 1937; 9: 432457.
  • 3
    Buckingham AD. Permanent and induced molecular moments and long-range intermolecular forces. Adv Chem Phys 1967; 12: 107142.
  • 4
    Eliel EL,Wilen SH,Mander LN. Stereochemistry of organic compounds. New York: Wiley; 1994, Chapter 13. p 9911118.
  • 5
    Harada N. Circular dichroism of twisted p-electron systems: theoretical determination of the absolute stereochemistry of natural products and chiral synthetic organic compounds. In: BerovaN,NakanishiK,WoodyRW, editors. Circular dichroism: principles and applications,2nd ed. New York: Wiley; 2000. p 431458.
  • 6
    Nakanishi K,Berova N. Exciton chirality method: principles and application. In: BerovaN,NakanishiK,WoodyRW, editors. Circular dichroism: principles and applications,2nd ed. New York: Wiley; 2000. p 337382.
  • 7
    Nafie LA,Freedman TB. Vibrational optical activity theory. In: BerovaN,NakanishiK,WoodyRW, editors. Circular dichroism: principles and applications,2nd ed. New York: Wiley; 2000. p 97132.
  • 8
    Stephens PJ. In: BultinckP,De WinterH,LangenaeckerW,TollenaereJ, editors. Computational medicinal chemistry for drug discovery. New York: Dekker; 2003, Chapter 26. p 699725.
  • 9
    Koslowski A,Sreerama N,Woody RW. Theoretical approach to electronic optical activity. In: BerovaN,NakanishiK,WoodyRW, editors. Circular dichroism: principles and applications,2nd ed. New York: Wiley; 2000. p 5595.
  • 10
    Polavarapu PL. Optical rotation: recent advances in determining the absolute configuration. Chirality 2002; 14: 768781.
  • 11
    Pecul M,Ruud K. The ab initio calculation of optical rotation and electronic circular dichroism. Adv Quantum Chem 2005; 50: 185227.
  • 12
    Crawford TD. Ab initio calculation of molecular chiroptical properties. Theor Chem Acc 2006; 115: 227245.
  • 13
    Polavarapu PL. Renaissance in chiroptical spectroscopic methods for molecular structure determination. Chem Rec 2007; 7: 125136.
  • 14
    Crawford TD,Tam MC,Abrams ML. The current status of ab initio calculations of optical rotation and electronic circular dichroism spectra. J Phys Chem A 2007; 14: 1205712068.
  • 15
    Frisch MJ,Trucks GW,Schiegel HB,Scuseria GE,Robb MA,Cheeseman JR,Zakrzewski VG,Montgomery JAJr.,Stratmann RE,Burant JC,Dapprich S,Milliam JM,Daniels AD,Kudin KN,Strain MC,Farkas O,Tomasi J,Barone V,Cossi M,Cammi R,Mennucci B,Pomelli C,Adamo C,Clifford S,Ochterski J,Petersson GA,Ayala PY,Cul Q,Morokuma K,Malick DK,Rabuck AD,Raghavachari K,Foresman JB,Closiowski J,Ortiz JV,Stefanov BB,Liu G,Liashenko A,Piskorz P,Komaromi I,Gomperts R,Martin RL,Fox DJ,Keith T,Al-Laham MA,Peng CY,Nanayakkara A,Gonzalez C,Challacombe M,Gill PMW,Johnson BG,Chen W,Wong MW,Andres JL,Head-Gorden M,Replogie ES,Pople JA. Gaussian 03. Pittsburgh, PA: Gaussian, Inc.; 2003, http://ww.gaussian.com/
  • 16
    Helgaker T,Jensen HJ Aa,Joergensen P,Olsen J,Ruud K,Aagren H,Auer AA,Bak KL,Bakken V,Christiansen O,Coriani S,Dahle P,Dalskov EK,Enevoldsen T,Fernandez B,Haettig C,Haid K,Halkier A,Helberg H,Hettema H,Jonsson D,Kirpekar S,Kobayashi R,Koch M,Mikkelsen KV,Norman P,Packer MJ,Pedersen TB,Ruden TA,Sanchez A,Saue T,Sauer SPA,Schimmelpfennig B,Sylvester-Hvid KO,Taylor PR,Vahtras O.Dalton. A molecular electronic structure program, Release 2.0 ( 2005),http://www.dalton-program.org.
  • 17
    Ahlrichs R,Bar M,Baron H-P,Bauernschmitt R,Bocker S,Ehrig M,Eichkorn K,Elliott S,Furche F,Haase F,Haser M,Horn H,Hattig C,Huber C,Huniar U,Kattannek M,Kohn A,Kolmes C,Kollwitz M,May K,Ochsenfeld C,Öhm H,Schafer A,Schneider U,Treutler O,Arnim MV,Weigend F,Weis P,Weiss H. TURBOMOLE, version 5.10. Universitat Karlsruhe: Karlsruhe; Germany, 2008.
  • 18
    Stephens PJ,Devlin FJ,Cheeseman JR,Frisch MJ. Calculation of optical rotation using density functional theory. J Phys Chem A 2001; 105: 53565371.
  • 19
    Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 56485652.
  • 20
    Lee C,Yang W,Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785789.
  • 21
    Stephens PJ,Devlin FJ,Chabalowski CF,Frisch MJ. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 1994; 98: 1162311627.
  • 22
    Cheeseman JR,Frisch MJ,Devlin FJ,Stephens PJ. Hartree-Fock and density functional theory ab initio calculation of optical rotation using GIAOs: basis set dependence. J Phys Chem A 2000; 104: 10391046.
  • 23
    Stephens PJ,Devlin FJ,Cheeseman JR,Frisch MJ,Mennucci B,Tomasi J. Prediction of optical rotation using density functional theory: 6,8-dioxabicyclo[3.2.1]octanes. Tetrahedron: Asymmetry 2000; 11: 24432448.
  • 24
    Stephens PJ,Devlin FJ,Cheeseman JR,Frisch MJ. Ab initio prediction of optical rotation: comparison of density functional theory and Hartree-Fock methods for three 2,7,8-trioxabicyclo[3.2.1]octanes. Chirality 2002; 14: 288296.
  • 25
    Mennucci B,Tomasi J,Cammi R,Cheeseman JR,Frisch MJ,Devlin FJ,Gabriel S,Stephens PJ. Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J Phys Chem A 2002; 106: 61026113.
  • 26
    Stephens PJ,Devlin FJ,Cheeseman JR,Frisch MJ,Rosini C. Determination of absolute configuration using optical rotation calculated using density functional theory. Org Lett 2002; 4: 45954598.
  • 27
    Stephens PJ,Devlin FJ,Cheeseman JR,Frisch MJ,Bortolini O,Besse P. Determination of absolute configuration using ab initio calculation of optical rotation. Chirality 2003; 15( Suppl): S57S64.
  • 28
    Stephens PJ,Mccann DM,Butkus E,Stoncius S,Cheeseman JR,Frisch MJ. 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 2004; 69: 19481958.
  • 29
    Stephens PJ,Mccann DM,Devlin FJ,Cheeseman JR,Frisch MJ. Determination of the absolute configuration of (1,4)barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J Am Chem Soc 2004; 126: 75147521.
  • 30
    Mccann DM,Stephens PJ,Cheeseman JR. Determination of absolute configuration using density functional theory calculation of optical rotation: chiral alkanes. J Org Chem 2004; 69: 87098717.
  • 31
    Stephens PJ,Mccann DM,Cheeseman JR,Frisch MJ. 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 2005; 17( Suppl): S52S64.
  • 32
    Mccann DM,Stephens PJ. Determination of absolute configuration using density functional theory calculations of optical rotation and electronic circular dichroism: chiral alkenes. J Org Chem 2006; 71: 60746098.
  • 33
    Autschbach J,Jensen L,Schatz GC,Electra Tse YC,Krykunov M. Time-dependent density functional calculations of optical rotatory dispersion including resonance wavelengths as a potentially useful tool for determining absolute configurations of chiral molecules. J Phys Chem A 2006; 110: 24612473.
  • 34
    Da Silva C,Mennucci B. The optical rotation of glucose prototypes: a local or global property? J Chem Theory Comput 2007; 3: 6270.
  • 35
    Stephens PJ,Mccann DM,Devlin FJ,Flood TC,Butkus E,Stoncius S,Cheeseman JR. Determination of molecular structure using vibrational circular dichroism spectroscopy: the keto-lactone product of Baeyer-Villiger oxidation of (+)-(1R,5S)-bicyclo[3.3.1]nonane-2,7-dione. J Org Chem 2005; 70: 39033913.
  • 36
    Stephens PJ,Mccann DM,Devlin FJ,Smith AB. Determination of the absolute configurations of natural products via density functional theory calculations of optical rotation, electronic circular dichroism, and vibrational circular dichroism: the cytotoxic sesquiterpene natural products quadrone, suberosenone, suberosanone, and suberosenol A acetate. J Nat Prod 2006; 69: 10551064.
  • 37
    Stephens PJ,Pan JJ,Devlin FJ,Krohn K,Kurtan T. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the iridoids plumericin and isoplumericin. J Org Chem 2007; 72: 35213536.
  • 38
    Stephens PJ,Pan JJ,Devlin FJ,Urbanovà M,Hajicek J. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism and optical rotation: the schizozygane alkaloid schizozygine. J Org Chem 2007; 72: 25082524.
  • 39
    Krohn K,Gehle D,Dey SK,Nahar N,Mosihuzzaman M,Sultana N,Sohrab MH,Stephens PJ,Pan JJ,Sasse F. Prismatomerin, a New Iridoid from Prismatomeris tetrandra. Structure elucidation, determination of absolute configuration, and cytotoxicity. J Nat Prod 2007; 70: 13391343.
  • 40
    Stephens PJ,Devlin FJ,Gasparrini F,Ciogli A,Spinelli D,Cosimelli B. Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation. J Org Chem 2007; 72: 47074715.
  • 41
    Polavarapu PL,He J,Crassous J,Ruud K. Absolute configuration of C76 from optical rotatory dispersion. ChemPhysChem 2005; 6: 25352540.
  • 42
    Petrovic AG,He J,Polavarapu PL,Xiao LS,Armstrong DW. Absolute configuration and predominant conformations of 1,1-dimethyl-2-phenylethyl phenyl sulfoxide. Org Biomol Chem 2005; 3: 19771981.
  • 43
    Petrovic AG,Polavarapu PL,Drabowicz J,Zhang Y,Mcconnell OJ,Duddeck H. Absolute configuration of C2-symmetric spiroselenurane: 3,3,3′,3′-tetramethyl-1,1′-spirobi[3 H,2,1]benzoxaselenole. Chem Eur J 2005; 11: 42574262.
  • 44
    Petrovic AG,Polavarapu PL. Chiroptical spectroscopic determination of molecular structures of chiral sulfinamides: t-butanesulfinamide. JPhys Chem A 2007; 111: 1093810943.
  • 45
    Armstrong DW,Cotton FA,Petrovic AG,Polavarapu PL,Warnke MM. Resolution of enantiomers in solution and determination of the chirality of extended metal atom chains. Inorg Chem 2007; 46: 15351537.
  • 46
    Zuber G,Goldsmith MR,Hopkins TD,Beratan DN,Wipf P. systematic assignment of the configuration of flexible natural products by spectroscopic and computational methods: the bistramide C analysis. Org Lett 2005; 7: 52695272.
  • 47
    Zuber G,Goldsmith MR,Beratan DN,Wipf P. Assignment of the absolute configuration of [n]-ladderanes by TD-DFT optical rotation calculations. Chirality 2005; 17: 507510.
  • 48
    Marchesan D,Coriani S,Forzato C,Nitti P,Pitacco G,Ruud K. Optical rotation calculation of a highly flexible molecule: the case of paraconic acid. J Phys Chem A 2005; 109: 14491453.
  • 49
    Forzato C,Furlan G,Nitti P,Pitacco G,Marchesan D,Coriani S,Valentin E. A combined experimental and computational strategy in the assignment of absolute configurations of 4-methyl-5-oxo-tetrahydrofuran-3-carbozylic acids and their esters. Tetrahedron: Asymmetry 2005; 16: 30113023.
  • 50
    Cheng M,Li Q,Lin B,Sha Y,Ren J,He Y,Wang Q,Hua H,Ruud K. Assignment of the absolute configuration of (−)-linarinic acid by theoretical calculation and asymmetric total synthesis. Tetrahedron: Asymmetry 2006; 17: 179183.
  • 51
    Voloshina E,Fleischhauer J,Kraft P. Conformational analysis and CD calculations of methyl-substituted 13-tridecano-13-lactones. Helv Chim Acta 2005; 88: 194209.
  • 52
    Seibert S,Konig GM,Voloshina E,Raabe G,Fleischhauer J. An attempt to determine the absolute configuration of two ascolactone stereoisomers with time-dependent density functional theory. Chirality 2006; 18: 413418.
  • 53
    Grimme S. Calculation of frequency dependent optical rotation using density functional response theory. Chem Phys Lett 2001; 339: 380388.
  • 54
    Grimme S,Furche F,Ahlrichs R. An improved method for density functional calculations of the frequency-dependent optical rotation. Chem Phys Lett 2002; 361: 321328.
  • 55
    Grimme S,Bahlmann A,Haufe G. Ab initio calculations for the optical rotations of conformationally flexible molecules: a case study on six-, seven-, and eight-membered fluorinated cycloalkanol esters. Chirality 2002; 14: 793797.
  • 56
    Pescitelli G,Di Bari L,Caporusso AM,Salvadori P. The prediction of the circular dichroism of the benzene chromophore: TDDFT calculations and sector rules. Chirality 2008; 20: 393399.
  • 57
    Hussain H,Akhtar N,Draeger S,Schulz B,Pescitelli G,Salvadori P,Antus S,Kurtan T,Krohn K. New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. From Laurus azorica. Eur J Org Chem 2009; 749756.
  • 58
    Giorgio E,Minichino C,Viglione RG,Zanasi R,Rosini C. Assignment of the molecular absolute configuration through the ab initio Hartree-Fock calculation of the optical rotation: can the circular dichroism data help in reducing basis set requirements?. J Org Chem 2003; 68: 51865192.
  • 59
    Giorgio E,Rosini C,Viglione RG,Zanasi R. Calculation of the gas phase specific rotation of (S)-propylene oxide at 355 nm. Chem Phys Lett 2003; 376: 452456.
  • 60
    Giorgio E,Viglione RG,Rosini C. Assignment of the absolute configuration of large molecules by ab initio calculation of the rotatory power within a small basis set scheme: the case of some biologically active natural products. Tetrahedron: Asymmetry 2004; 15: 19791986.
  • 61
    Giorgio E,Viglione RG,Zanasi R,Rosini C. Ab Initio calculation of optical rotatory dispersion (ORD) curves: a simple and reliable approach to the assignment of the molecular absolute configuration. J Am Chem Soc 2004; 126: 1296812976.
  • 62
    Giorgio E,Tanaka K,Ding W,Krishnamurthy G,Pitts K,Ellestad GA,Rosini C,Berova N. Theoretical simulation of the electronic circular dichroism spectrum of calicheamicin. Bioorg Med Chem 2005; 13: 50725079.
  • 63
    Giorgio E,Roje M,Tanaka K,Hamersak Z,Sunjic V,Nakanishi K,Rosini C,Berova N. Determination of the absolute configuration of flexible molecules by ab initio ORD calculations: a case study with cytoxazones and isocytoxazones. J Org Chem 2005; 70: 65576563.
  • 64
    Giorgio E,Tanaka K,Verotta L,Nakanishi K,Berova N,Rosini C. Determination of the absolute configurations of flexible molecules: synthesis and theoretical simulation of electronic circular dichroism/optical rotation of some pyrrolo[2,3-b]indoline alkaloids—a case study. Chirality 2007; 19: 434445.
  • 65
    Mennucci B,Claps M,Evidente A,Rosini C. Absolute configuration of natural cyclohexene oxides by time dependent density functional theory calculation of the optical rotation: the absolute configuration of (−)-sphaeropsidone and (−)-episphaeropsidone revised. J Org Chem 2007; 72: 66806691.
  • 66
    Tartaglia S,Padula D,Scafato P,Chiummiento L,Rosini C. A chemical/computational approach to the determination of the absolute configuration of flexible and transparent molecules: aliphatic diols as a case study. J Org Chem 2008; 73: 48654873.
  • 67
    Scarso A,Pellizzaro L,De Lucchi O,Linden A,Fabris F. Gas hosting in enantiopure self-assembled oximes. Angew Chem Int Ed 2007; 46: 49724975.
  • 68
    Fabris F,Pellizzaro L,Zonta C,De Lucchi O. A novel C3-symmetric triol as chiral receptor for ammonium ions. Eur J Org Chem 2007; 283291.
  • 69
    SPARTAN '02. Irvine, CA: Wavefunction Inc. Available at: http://www.wavefunction.com.
  • 70
    Ley SV,Norman J,Griffith WP,Marsden SP,Paquette LA,Hong FT. Tetrapropylammonium perruthenate, Pr4N+RuO4-TPAP—a catalytic oxidant for organic-synthesis. Synthesis 1994; 68: 639666.
  • 71
    Dauben WG,Gerdes J,Look GC. Organic reactions at high pressure. Conversion of cyclic alkanones and enones to 1,3-dioxolanes. J Org Chem 1986; 51: 49644970.
  • 72
    Borsato G,De Lucchi O,Fabris F,Groppo L,Lucchini V,Zambon A. Efficient cyclotrimerization of bicyclic vic-bromostannylalkenes promoted by copper(I) thiophen-2-carboxylate. J Org Chem 2002; 67: 78947897.
  • 73
    Fabris F,Bellotto L,De Lucchi O,Fabris F,Zambrini L,Rosso E,De Lucchi O. (+)-syn-Benzotriborneol: the first functionalised enantiopure C3-symmetric benzocyclotrimer. Tetrahedron Lett 2003; 44: 12111215.
  • 74
    Fabris F,Zambrini L,Rosso E,De Lucchi O. Comparative cyclotrimerization of enantiopure vic-bromotrimethyltinbicycloolefins derived from (+)-camphor, (+)-fenchocamphorone and (–)-epicamphor. Effect of the bridgehead methyl group in the syn to anti products ratio. Eur J Org Chem 2004; 33133322.
  • 75
    Kawamata J,Inoue K. New 2nd-Order nonlinear-optical materials with a cutoff wavelength of 350 nm - 3-benzylidene-D-camphor derivatives. Chem Lett 1993; 921924.
  • 76
    Tomasi J,Mennucci B,Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005; 105: 29993093.
  • 77
    Sandman D,Mislow K,Giddins WP,Dirlam J,Hanson GC. Stereochemistry of 2-benznorbornenone. J Am Chem Soc 1968; 90: 48774884.
  • 78
    Moscowitz A. Theory and analysis of rotatory dispersion curves. In: DjerassiC, editor. Optical rotatory dispersion: application to organic chemistry. New York: McGraw-Hill; 1960,Chapter 12. p 150177.
  • 79
    Polavarapu PL. Kramers-Kronig transformation for optical rotatory dispersion studies. J Phys Chem A 2005; 109: 70137023.
  • 80
    Smith HE. Applications of the benzene sector and benzene chirality rules. In: BerovaN,NakanishiK,WoodyRW, editors. Circular dichroism: principles and applications,2nd ed. New York: Wiley; 2000. p 459490.
  • 81
    Gawronski JK. Circular dichroism and stereochemistry of chiral conjugated cyclohexenones. Tetrahedron 1982; 38: 326.
  • 82
    Devoe H. Optical properties of molecular aggregates. I. Classical model of electronic absorption and refraction. J Chem Phys 1964; 41: 393400.
  • 83
    DeVoe H. Optical properties of molecular aggregates. II. Classical theory of the refraction, absorption, and optical activity of solutions and crystals. J Chem Phys 1965; 43: 31993208.
  • 84
    Rosini C,Salvadori P,Zandomeneghi M. Coupled oscillator calculations of circular dichroism intensities: structural applications in organic chemistry. Tetrahedron: Asymmetry 1993; 4: 545554.
  • 85
    Superchi S,Giorgio E,Rosini C. Structural determinations by circular dichroism spectra analysis using coupled oscillator methods: an update of the applications of the DeVoe polarizability model. Chirality 2004; 16: 422451.