General Semiempirical Quantum Mechanical Solvation Model for Nonpolar Solvation Free Energies. n-Hexadecane

Giesen, David J.; Storer, Joey W.; Cramer, Christopher J.; Truhlar, Donald G.

doi:10.1021/ja00108a023

Cited by 103 publications

(129 citation statements)

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“…For instance, polymerization of 4-(S)-isobutoxycarbonyl-2-azetidinone in DMSO renders the corresponding poly(~-L-aspartate) in 68% yield in about 5 min, whereas several days are required to obtain similar results if the reaction is conducted in DCM. Unfortunately, SCRF calculations in DMSO and DCM solvents cannot be performed since rigorous parameterizations for nonaqueous solvents are available only for alkanes [47], CHCI 3 [48], and COl 4 [21].…”

Section: Comparison Of Theoretical and Experimental Datamentioning

confidence: 99%

“…In a systematic study of the polimerizabilities of a variety of alkyl-~-lactams, Bestian [49] found that the L~on, Aiem~n, Garcfa-Alvarez, and Mufioz-Guerra polymerization of these compounds leading to the formation of poly(~-amide)s proceeded faster for I than for III and that, in general, the reaction rate decreased when the number of substituents on the ring increased [47]. This behavior is commonly interpreted in terms of entropic effects which are known to be less favorable for substituted compounds.…”

Section: Comparison Of Theoretical and Experimental Datamentioning

confidence: 99%

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Theoretical study of the conformational and electrostatic properties of C4-monosubstituted 2-azetidinones

et al. 1997

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The conformational preferences and electrostatic properties of 2-azetidinone, 4-(S)-methoxycarbonyl-2-azetidinone and 4-(R)-methyl-2-azetidinone have been studied in gas-phase, aqueous solution and CC14 solution using quantum mechanical methods. Gas-phase calculations were performed at the ab initio HF, MP2, and MP4 levels and solvent effects were investigated using a self-consistent reaction-field procedure adapted to the AM I Hamiltonian. An almost planar arrangement was adopted by the/3-1actam ring in the three cases, whereas the alkoxycarbonyl side group was found to display a large conformational flexibility. The effects of the different solvents on the electrostatic properties of the three compounds were investigated by following the changes in both molecular electrostatic potentials and induced dipole moments. The resulting electrostatic parameters were used as static reactivity indices to predict the response of the systems to the attack of nucleophilic reagents. Theoretical results were compared with experimental data available on the structure and properties of/3-1actams. The validity of the method as a predicting tool was critically discussed.

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Section: Comparison Of Theoretical and Experimental Datamentioning

confidence: 99%

Section: Comparison Of Theoretical and Experimental Datamentioning

confidence: 99%

Theoretical study of the conformational and electrostatic properties of C4-monosubstituted 2-azetidinones

et al. 1997

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“…The first SM4 model to be reported was not for water as solvent, but instead for n-hexadecane [94] (a solvent for which many data are available because it can be used as a stationary phase in capillary gas chromatography). For the hexadecane model, another new feature was also introduced into the SM4 model, namely, the use of different solvent radii to compute solvent accessible surface areas associated with different physical components of the CDS term.…”

Section: Smx Models For Semiempirical Hamiltoniansmentioning

confidence: 99%

SMx Continuum Models for Condensed Phases

Cramer

Truhlar

2006

Trends and Perspectives in Modern Computational Science

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Abstract:The SMx continuum models are designed to include condensed-phase effects in classical and quantum mechanical electronic structure calculations and can also be used for calculating geometries and vibrational frequencies in condensed phases. Originally developed for homogeneous liquid solutions, the SMx models have seen substantial application to more complicated condensed phases as well, e.g., the airwater interface, soil, phospholipid membranes, and vapor pressures of crystals as well as liquids. Bulk electrostatics are accounted for via a generalized Born formalism, and other physical contributions to free energies of interaction between a solute and the surrounding condensed phase are modeled by environmentally sensitive atomic surface tensions associated with solute atoms having surface area exposed to the surrounding medium. The underlying framework of the models, including the charge models used for the electrostatics, and some of the models' most recent extensions are summarized in this report. In addition, selected applications to environmental chemistry problems are presented.

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“…The value of 2·8 Å is more popular for the thickness of the water solvent shell, 16 and this value was adopted in this study. For ab initio GB calculations, the 6-31 + + G* basis set was used.…”

Section: Theory and Calculationmentioning

confidence: 99%

Ab Initio Mo and Monte Carlo Simulation Study on the Conformation Ofl-Alanine Zwitterion in Aqueous Solution

Kikuchi¹,

Watanabe²,

Ogawa³

et al. 1997

J. Phys. Org. Chem.

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General Semiempirical Quantum Mechanical Solvation Model for Nonpolar Solvation Free Energies. n-Hexadecane

Cited by 103 publications

References 1 publication

Theoretical study of the conformational and electrostatic properties of C4-monosubstituted 2-azetidinones

Theoretical study of the conformational and electrostatic properties of C4-monosubstituted 2-azetidinones

SMx Continuum Models for Condensed Phases

Ab Initio Mo and Monte Carlo Simulation Study on the Conformation Ofl-Alanine Zwitterion in Aqueous Solution

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