Development of a virtual spectrometer for chiroptical spectroscopies: The case of nicotine

Chirality

Volumn 25, Issue 11, 2013, Pages 701-708

  Egidi, Franco ^a   Bloino, Julien ^a,b   Cappelli, Chiara ^a,c   Barone, Vincenzo ^a  

^a SCUOLA NORMALE SUPERIORE   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

nicotine; optical rotation; vibrational circular dichroism; virtual spectrometers

Indexed keywords

NICOTINE;

ARTICLE; CHIROPTICAL SPECTROSCOPY; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; OPTICAL ROTATION; PRIORITY JOURNAL; SOLVENT EFFECT; SPECTROMETER; SPECTROSCOPY; VIRTUAL SPECTROMETER;

NICOTINE; OPTICAL ROTATION; VIBRATIONAL CIRCULAR DICHROISM; VIRTUAL SPECTROMETERS;

MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICOTINE; OPTICAL PROCESSES; SOLVENTS; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 84886640074     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22200     Document Type: Article

References (60)

1. Berova N, Polavarapu PL, Nakanishi K, Woody RW,. Comprehensive chiroptical spectroscopy. Hoboken, NJ: John Wiley & Sons; 2011.
2. Nafie LA,. Vibrational optical activity: principles and applications. New York: John Wiley & Sons; 2001.
3. Stephens PJ, Devlin FJ, Cheeseman JR,. VCD spectroscopy for organic chemists. New York: John Wiley & Sons; 2001.
4. Barone V,. Computational strategies for spectroscopy. Hoboken, NJ: John Wiley & Sons; 2012.
5. Barone V, Improta R, Rega N,. Quantum mechanical computations and spectroscopy: from small rigid molecules in the gas phase to large flexible molecules in solution. Acc Chem Res 2008; 41: 605-616.
6. Barone V, Baiardi A, Biczysko M, Bloino J, Cappelli C, Lipparini F,. Implementation and validation of a multi-purpose virtual spectrometer for large systems in complex environments. Phys Chem Chem Phys 2012; 14: 12 404-12 422.
7. Bloino J, Barone V,. A second-order perturbation theory route to vibrational averages and transition properties of molecules: general formulation and application to infrared and vibrational circular dichroism spectroscopies. J Chem Phys 2012; 136: 124 108.
8. Elmore DE, Dougherty DA,. A computational study of nicotine conformations in the gas phase and in water. J Org Chem 2000; 65: 742-747.
9. Takeshima T, Fukumoto R, Egawa T, Konaka S,. Molecular structure of nicotine as studied by gas electron diffraction combined with theoretical calculations. J Phys Chem A 2002; 106: 8734-8740.
10. Mora M, Castro ME, Nino A, Melendez FJ, Munoz-Caro C,. Analysis of B3LYP and MP2 conformational population distributions in trans-nicotine, acetylcholine, and ABT-594. Int J Quantum Chem 2005; 103: 25-33.
11. Munoz-Caro C, Nino A, Mora M, Reyes S, Melendez FJ, Castro ME,. Conformational population distribution of acetylcholine, nicotine and muscarine in vacuum and solution. J Mol Struc-THEOCHEM 2005; 726: 115-124.
12. Whidby JF, Edwards WB III, Pitner TP,. Isomeric nicotines. Their solution conformation and proton, deuterium, carbon-13, and nitrogen-15 nuclear magnetic resonance. J Org Chem 1979; 44: 794-798.
13. Testa B, Jenner P,. Circular dichroic determination of the preferred conformation of nicotine and related chiral alkaloids in aqueous solution. Mol Pharm 1972; 9: 10-16.
14. Clayton PM, Vas CA, Bui TTT, Drake AF, McAdam K,. Spectroscopic investigations into the acid-base properties of nicotine at different temperatures. Anal Methods 2013; 5: 81-88.
15. Baranska M, Dobrowolski JC, Kaczor A, Chruszcz-Lipska K, Gorza K, Rygula A,. Tobacco alkaloids analyzed by Raman spectroscopy and DFT calculations. J Raman Spectrosc 2012; 43: 1065-1073.
16. Tomasi J, Mennucci B, Cammi R,. Quantum mechanical continuum solvation models. Chem Rev 2005; 105: 2999-3093.
17. Mennucci B,. Polarizable continuum model. WIREs Comput Mol Sci 2012; 2: 386-404.
18. Cammi R, Mennucci B,. Continuum solvation models in chemical physics. Hoboken, NJ: John Wiley & Sons; 2007.
19. Frediani L, Cammi R, Corni S, Tomasi J,. A polarizable continuum model for molecules at diffuse interfaces. J Chem Phys 2004; 120: 3893-3907.
20. Mennucci B, Caricato M, Ingrosso F, Cappelli C, Cammi R, Tomasi J, Scalmani G, Frisch MJ,. How the environment controls absorption and fluorescence spectra of PRODAN: a quantum-mechanical study in homogeneous and heterogeneous media. J Phys Chem B 2008; 112: 414-423.
21. Corni S, Tomasi J,. Enhanced response properties of a chromophore physisorbed on a metal particle. J Chem Phys 2001; 114: 3739-3751.
22. Bertoldo M, Bronco S, Cappelli C, Gragnoli T, Andreotti L,. Combining theory and experiment to study the photooxidation of polyethylene and polypropylene. J Phys Chem B 2003; 107: 11 880-11 888.
23. Onsager L,. Electric moments of molecules in liquids. J Am Chem Soc 1936; 58: 1486-1493.
24. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ,. Calculation of optical rotation using density functional theory. J Phys Chem A 2001; 105: 5356-5371.
25. Cammi R, Cappelli C, Corni S, Tomasi J,. On the calculation of infrared intensities in solution within the polarizable continuum model. J Phys Chem A 2000; 104: 9874-9879.
26. Barron L,. Molecular light scattering and optical activity, 2nd ed. New York: Cambridge University Press; 2004.
27. Cappelli C, Corni S, Cammi R, Mennucci B, Tomasi J,. Nonequilibrium formulation of infrared frequencies and intensities in solution. J Chem Phys 2000; 113: 11 270-11 279.
28. Cappelli C, Corni S, Tomasi J,. Vibrational circular dichroism within the polarizable continuum model. J Chem Phys 2001; 115: 5531-5535.
29. Cappelli C, Lipparini F, Bloino J, Barone V,. Towards an accurate description of anharmonic infrared spectra in solution within the polarizable continuum model: reaction field, cavity field and nonequilibrium effects. J Chem Phys 2011; 135: 104505.
30. Epstein ST,. Gauge invariance of the Hartree-Fock approximation. J Chem Phys 1965; 42: 2897-2898.
31. Ditchfield R,. Self-consistent perturbation theory of diamagnetism. Mol Phys 1974; 27: 789-807.
32. 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: 1039-1046.
33. Cammi R,. The Hartree-Fock calculation of the magnetic properties of molecular solutes. J Chem Phys 1998; 109: 3185-3196.
34. 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: 6102-6113.
35. Ruud K, Taylor PR, Astrand PO,. Zero-point vibrational effects on optical rotation. Chem Phys Lett 2001; 337: 217-223.
36. Ruud K, Zanasi R,. The importance of molecular vibrations: The sign change of the optical rotation of methyloxirane. Angew Chem Int Ed 2005; 44: 3594-3596.
37. Kongsted J, Pedersen TB, Jensen L, Hansen AE, Mikkelsen KV,. Coupled cluster and density functional theory studies of the vibrational contribution to the optical rotation of (S)-propylene oxide. J Am Chem Soc 2006; 128: 976-982.
38. Kongsted J, Ruud K,. Solvent effects on zero-point vibrational corrections to optical rotations and nuclear magnetic resonance shielding constants. Chem Phys Lett 2008; 451: 226-232.
39. Auer AA, Gauss J, Stanton JF,. Quantitative prediction of gas-phase shielding constants 13C nuclear magnetic shielding constants. J Chem Phys 2003; 118: 10 407-10 417.
40. Grigoleit S, BuÂ̈hl M,. Thermal effects and vibrational corrections to transition metal NMR chemical shifts. Chem Eur J 2004; 10: 5541-5552.
41. Mort BC, Autschbach J,. Magnitude of zero-point vibrational corrections of optical rotation in rigid organic molecules. J Phys Chem A 2005; 109: 8617-8623.
42. Barone V,. Accurate vibrational spectra of large molecules by Density Functional computations beyond the harmonic approximation: the case of azabenzenes. J Phys Chem A 2004; 108: 4146-4150.
43. Barone V,. Anharmonic vibrational properties by a fully automated second-order perturbative approach. J Chem Phys 2005; 122: 014 108.
44. Egidi F, Bloino J, Barone V, Cappelli C,. Toward an accurate modeling of optical rotation for solvated systems: Anharmonic vibrational contributions coupled to the polarizable continuum model. J Chem Theory Comput 2012; 8: 585-597.
45. Mennucci B, Cappelli C, Cammi R, Tomasi J,. Modeling solvent effects on chiroptical properties. Chirality 2011; 23: 717-729.
46. Cappelli C, Monti S, Scalmani G, Barone V,. On the calculation of vibrational frequencies for molecules in solution beyond the harmonic approximation. J Chem Theory Comput 2010; 6: 1660-1669.
47. Cappelli C, Bloino J, Lipparini F, Barone V,. Towards ab-initio anharmonic vibrational circular dichroism spectra in the condensed phase. J Phys Chem Lett 2012; 3: 1766-1773.
48. Barone V, Bloino J, Guido CA, Lipparini F,. A fully automated implementation of VPT2 infrared intensities. Chem Phys Lett 2010; 496: 157-161.
49. Bloino J, Biczysko M, Barone V,. General perturbative approach for spectroscopy, thermodynamics, and kinetics: methodological background and benchmark studies. J Chem Theory Comput 2012; 8: 1015-1036.
50. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ,. Gaussian Development Version Revision H.28. Wallingford, CT: Gaussian Inc.; 2009.
51. Becke AD,. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 5648-5652.
52. 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: 785-789.
53. Barone V, Cimino P, Stendardo E,. Development and validation of the B3LYP/N07D computational model for structural parameter and magnetic tensors of large free radicals. J Chem Theory Comput 2008; 4: 751-764.
54. Barone V, Biczysko M, Bloino J, Puzzarini C,. Glycine conformers: a never-ending story? Phys Chem Chem Phys 2013; 15: 1358-1363.
55. Cappelli C, Corni S, Mennucci B, Cammi R, Tomasi J,. Vibrational circular dichroism within the polarizable continuum model. J Phys Chem A 2002; 106: 12 331-12 339.
56. Mennucci B, Cammi R, Tomasi J,. Excited states and solvatochromic shifts within a nonequilibrium solvation approach. J Chem Phys 1998; 109: 2798-2807.
57. Tomasi J, Persico M,. Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem Rev 1994; 94: 2027-2094.
58. Marenich AV, Cramer CJ, Truhlar DG,. Universal solvation model based on solute electron density and a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 2009; 113: 6378-6396.
59. Lipparini F, Egidi F, Cappelli C, Barone V,. The optical rotation of methyloxirane in aqueous solution: a never ending story? J Chem Theory Comput 2013; 9: 1880-1884.
60. Infrared spectrum from the Bio-Rad/Sadtler IR Data collection. Obtained from Bio-Rad Laboratories, Philadelphia, PA.