Ab initio studies on conformation, vibrational and electronic spectra of methyl methacrylate

Virdi, Ajit; Gupta, Vikram; Sharma, Atul

doi:10.1016/s0166-1280(03)00244-6

Cited by 15 publications

(6 citation statements)

References 16 publications

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“…8 kcal mol -1 ). [45,46] In the lactate monocomplexes (ML) this energy difference remains similar. In the acryloyl monocomplexes (MA), however, as well as in the 2:1 complexes (M2), the s-cis conformers are practically isoenergetic with the s-trans ones, without any significant change in the activation free energy for interconversion.…”

Section: Ligand Coordinationmentioning

confidence: 87%

A Theoretical Study of the Stereoselectivities of the Diels–Alder Addition of Cyclopentadiene to Ethyl‐(S)‐lactyl Acrylate Catalyzed by Aluminium Chloride

Bakalova

Santos

2006

Eur J Org Chem

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We have studied the AlCl 3 -catalyzed cycloaddition of ethyl-(S)-lactyl acrylate (ELA) and cyclopentadiene (CPD) by MP2 and DFT (B3LYP) methods using the 6-31G(d,p) basis set, with or without solvent effects. Four types of dienophileLewis acid (LA) complexes were considered − two types of ELA·AlCl 3 , ELA·2AlCl 3 and ELA·AlCl 2 + . The stereochemical predictions of these models were compared with available experimental data. The participation of lactate-bound ELA·AlCl 3 complexes is insignificant because of their relatively high TS energies. The diastereofacial selectivities exhibited by the chelated ELA·AlCl 2 + complex do not agree

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Section: Ligand Coordinationmentioning

confidence: 87%

A Theoretical Study of the Stereoselectivities of the Diels–Alder Addition of Cyclopentadiene to Ethyl‐(S)‐lactyl Acrylate Catalyzed by Aluminium Chloride

Bakalova

Santos

2006

Eur J Org Chem

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“…Baker et al [13] have suggested certain scaling factors for RHF frequencies. These have been used in the present case with certain modifications based on our experience with unsaturated ester molecules [8,9]. Thus, scaling factors for single bonded torsion and X-X-X bend (X refers to non-hydrogen atoms) have been taken as 0.905 and 0.912, respectively, as against 0.913 and 0.990 suggested by Baker et al [13].…”

Section: Vibrational Analysismentioning

confidence: 99%

“…Some such studies on a series of compounds like methyl acrylate [7], methyl methacrylate [8], and methyl trans crotonate [9], which are two rotor systems, having the possibility of rotational isomerism about C-O and C-C single bonds, have been undertaken in this laboratory using spectroscopic and quantum chemical techniques. In contrast to these molecules, methyl-3-methoxy-2-propenoate (MMP) has the possibility of rotational isomerism about three bonds (two C-O and one C-C) and may have a more complex structure.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of structure, vibrational and electronic spectra of isomers of methyl-3-methoxy-2-propenoate

2004

Self Cite

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Abstract:A systematic quantum mechanical study of the possible conformations, their relative stabilities, vibrational and electronic spectra and thermodynamic parameters of methyl-3-methoxy-2-propenoate has been reported for the electronic ground (S 0 ) and first excited (S 1 ) states using time-dependent and time-independent Density Functional Theory (DFT) and RHF methods in extended basis sets. Detailed studies have been restricted to the E-isomer, which is found to be substantially more stable than the Z-isomer. Four possible conformers c Cc, c Tc, t Cc, t Tc, of which the first two are most stable, have been identified in the S 0 and S 1 states. Electronic excitation to S 1 state is accompanied with a reversal in the relative stability of the c Cc and c Tc conformers and a substantial reduction in the rotational barrier between them, as compared with the S 0 state. Optimized geometries of these conformers in the S 0 and S 1 states are being reported. Based on suitably scaled RHF/6-31G** and DFT/6-311G** calculations, assignments have been provided to the fundamental vibrational bands of both these conformers in terms of frequency, form and intensity of vibrations and potential energy distribution across the symmetry coordinates in the S 0 state. A complete interpretation of the electronic spectra of the conformers has been provided.

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“…Many reports, experimental [16][17][18][19][20][21] and theoretical [20,22], show that acrylates and related compounds exhibit rotational isomerism with the planar s-trans and s-cis heavyatom structures being the energetically most stable conformations. However, uncertainty continues to exist regarding the relative stability of the two conformers.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure and Vibrational Spectra of 2-Ethylhexyl Acrylate by Density Functional Theory Calculations

Belaidi

Bouchaour

Maschke

2013

Organic Chemistry International

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The Fourier transform infrared spectra (FTIR) of 2-ethylhexyl acrylate have been measured in liquid phase. The molecular geometry, vibrational frequencies, and infrared intensities have been calculated by using density functional theory. We found two local minima representing s-cis and s-trans conformations for 2-ethylhexyl acrylate molecule. The optimized geometries at DFT//B3LYP/6-311+ are in good agreement with electron diffraction data of methyl acrylate for the acrylic group. The two conformers were used for the interpretation of the experimental infrared spectrum of title compound. PED calculations are represented for a more complete and concise assignment. There is one band in the infrared spectrum at 1646 cm−1 that definitely indicates the conformer with s-trans arrangement of acrylic moiety to be present or not in the liquid 2-ethylhexyl acrylate.

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Ab initio studies on conformation, vibrational and electronic spectra of methyl methacrylate

Cited by 15 publications

References 16 publications

A Theoretical Study of the Stereoselectivities of the Diels–Alder Addition of Cyclopentadiene to Ethyl‐(S)‐lactyl Acrylate Catalyzed by Aluminium Chloride

A Theoretical Study of the Stereoselectivities of the Diels–Alder Addition of Cyclopentadiene to Ethyl‐(S)‐lactyl Acrylate Catalyzed by Aluminium Chloride

Theoretical study of structure, vibrational and electronic spectra of isomers of methyl-3-methoxy-2-propenoate

Molecular Structure and Vibrational Spectra of 2-Ethylhexyl Acrylate by Density Functional Theory Calculations

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