Determination of the structure of methylene cyclobutane confirming a non-planar ethene and the structure of the argon–methylene cyclobutane van der Waals complex

Lin, Wei; Gayle, Jovan A.; Pringle, Wallace C.; Novick, Stewart E.

doi:10.1016/j.jms.2008.02.019

Cited by 7 publications

(6 citation statements)

References 15 publications

(39 reference statements)

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“…On the contrary, the cyclobutane ring in exo-en isomer is puckered with C1-C2-C3-C4 and C2-C3-C4-C5 dihedral angles of 16.8 and 8.7 , respectively, using CCSD/aug-cc-PVDZ level of theory. The later results of exo-en are reported experimentally by Lin et al 5 with angle 1 between C2-C3-C4 plane and C3¼C5 bond of 6 , while C1-C2-C3-C4 dihedral angle 2 of 19.6 (see 1 and 2 in Fig. 2(b)).…”

Section: The Optimized Structuressupporting

confidence: 54%

“…4 A few studies on the structure and tautomerism of 1-methylcyclobutene to methylenecyclobutane (Scheme 1) have been reported. [5][6][7] The enthalpy and Gibbs free energy of this isomerization reaction have been reported to be 0.9 kcal/mol and 1.05 kcal/mol, respectively, with 1-methylcyclobutene being the more stable isomer. 7 Up to now, a limited number of thermodynamic studies have been carried out for the tautomerism of 1-methylcyclobutene to methylenecyclobutane.…”

Section: Introductionmentioning

confidence: 99%

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Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Alomari

Ababneh

Al‐Shboul

2017

J. Theor. Comput. Chem.

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In this study, geometrical optimizations, infrared spectroscopic analysis and relative stabilities of 1-methylcyclobutene and methylenecyclobutane tautomers were investigated by utilizing highlevel ab initio and DFT calculations. The thermodynamic data showed that 1-methylcyclobutene is the more stable isomer with enthalpy H $ 0:8 kcal/mol and Gibbs energy G $ 1:3 kcal/mol lower than that for methylenecyclobutane at the M06/aug-cc-PVTZ level of theory. These results are in good agreement with the available experimental data. Additionally, the geometrical parameters and vibrational frequencies agree well with the recorded results in literatures.

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Section: The Optimized Structuressupporting

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Alomari

Ababneh

Al‐Shboul

2017

J. Theor. Comput. Chem.

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“…Argon is further back on the ring and just inside the positively charged hydrogen on one of the equivalent cross-ring carbons. In the argon− methylene cyclobutane complex, 12 the argon is close to vdWs contact with the ring double-bonded carbon. It is also 0.1 Å further from vdWs contact with the hydrogen on C γ .…”

Section: ■ Introductionmentioning

confidence: 99%

Microwave Spectra and Structure of the Argon–Cyclopentanone and Neon–Cyclopentanone van der Waals Complexes

Lin¹,

Brooks

Minei

et al. 2014

J. Phys. Chem. A

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The rotational spectra of cyclopentanone and its van der Waals complexes with argon and neon have been observed with a Balle-Flygare type pulsed jet Fourier transform microwave spectrometer in the 6 to 20 GHz region. This work improves the rotational constants and quartic centrifugal distortion constants for cyclopentanone and its five (13)C and the (18)O isotopologues. The argon-(12)C5H8(16)O van der Waals complex has rotational constants of A = 2611.6688, B = 1112.30298, and C = 971.31969 MHz. The (20)Ne-(12)C5H8(16)O complex has rotational constants of A = 2728.8120, B = 1736.5882, and C = 1440.4681 MHz. In addition, the five unique, singly substituted (13)C and (18)O isotopologues of the argon complex are reported. The five single-substituted (13)C of the (20)Ne complex and the (22)Ne-(12)C5H8(16)O complex are reported. The rare gases are in van der Waals contact with the carbonyl α carbon and nearly in contact with the hydrogen on β and γ carbons toward the back of the ring.

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“…Cyclohexene oxide (CHO), 7-oxabicyclo[4,1,0]heptane, was first studied in the microwave region by Curl et al 1 who assigned spectra for the ground state and two excited states corresponding to the ring bending and twisting modes. They measured the dipole moments; μ a = 1.152 (6), μ b = 0.18 (8), and μ c = 1.52(1) D. The fact that there were three dipole components, and the magnitude, of the planar moment indicated to them the carbon ring is twisted, not planar. This was in agreement with earlier electron diffraction studies.…”

Section: ■ Introductionmentioning

confidence: 99%

Rotational Spectrum and Structure of Cyclohexene Oxide and the Argon–Cyclohexene Oxide van der Waals Complex

2013

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The rotational spectra of cyclohexene oxide and its van der Waals complex with argon have been observed with a Balle-Flygare type pulsed jet Fourier transform microwave spectrometer in the 6 to 20 GHz region. This work improves the existing rotational and quartic centrifugal distortion constants of cyclohexene oxide, its six singly substituted (13)C, and the (18)O isotopologue. In addition, the (17)O isotopologue was observed in natural abundance. The quadrupole coupling constants for the (17)O isotopologue are χ(aa) = 8.855(5), χ(bb) = -4.560(4), and χ(cc) = -4.296(4) MHz. The argon-(12)C6H10(16)O complex has rotational constants of A = 2146.4825(2), B = 908.64292(8), and C = 859.00320(8) MHz. Additionally, the six unique singly substituted (13)C isotopologues of the argon complex are reported here. The position of the argon that is consistent with the parent and six (13)C complex rotational constants is above the ring on the side opposite the epoxide.

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Determination of the structure of methylene cyclobutane confirming a non-planar ethene and the structure of the argon–methylene cyclobutane van der Waals complex

Cited by 7 publications

References 15 publications

Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Structure, vibrations and relative stability of 1-methylcyclobutene and methylenecyclobutane tautomers using DFT and CCSD methods

Microwave Spectra and Structure of the Argon–Cyclopentanone and Neon–Cyclopentanone van der Waals Complexes

Rotational Spectrum and Structure of Cyclohexene Oxide and the Argon–Cyclohexene Oxide van der Waals Complex

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