Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate

Matsumoto, Takatoshi; Kinoshita, Yoshio; Kasai, Yusuke; Kuwahara, Shunsuke; Watanabe, Masataka

doi:10.1016/j.tet.2006.11.017

Cited by 2 publications

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“…With respect to the intramolecular force stabilizing the so-called syn conformation, we have proposed the weak bifurcated hydrogen bond of triangular shape between O6-H8Ј-O7 (Figure 17) in both experimental [1] and theoretical [11] results. To check the weak bifurcated hydrogen bond [14,15] …”

Section: Weak Bifurcated Intramolecular Hydrogen Bond Between O6-h8ј-mentioning

confidence: 99%

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Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools

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To compare the crystalline-state conformations of MαNP acid esters with those existing in the solution state, X-ray crystallographic analyses of 22 MαNP esters and two MαNP acids were carried out. It was found that all 27 conformers observed in the solid state have structures in which the 2-CH 3 group and the 2Ј-H of the naphthyl group are synperiplanar and are almost always located in the same plane. In addition, the CH 3 -O7-C2-C1 moiety in all cases has an antiperiplanar structure within the MαNP plane. From further analyses, 22 conformers adopt the so-called syn structure, in which the O7-C2-C1-O6 moiety is synperiplanar. On the other hand, the remaining five conformers have the so-called anti structure. With regard to the rotational conformation around C1ЈЈ-O5, all conformers have structures similar to the synperiplanar conformation. In the so-called syn conformers, the interatomic distance d(H8Ј-O6) is distributed between 2.48 Å and 2.96 Å, while the distance d(H8Ј-O7) varies between 2.26 Å and 2.56 Å, indicating the weak bifurcated hydrogen

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Section: Weak Bifurcated Intramolecular Hydrogen Bond Between O6-h8ј-mentioning

confidence: 99%

“…The syn conformation of a MαNP ester is also supported by ab initio MO calculations. [11] Results and Discussion…”

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Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools

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A total conformational analysis of diastereomeric esters and calculation of their conformational shielding models

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Kreen

et al. 2008

Journal of Molecular Structure: THEOCHEM

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Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate

Cited by 2 publications

References 50 publications

Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools

Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools

A total conformational analysis of diastereomeric esters and calculation of their conformational shielding models

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Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate

Cited by 2 publications

References 50 publications

Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral 1H NMR Anisotropy Tools

Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral 1H NMR Anisotropy Tools

A total conformational analysis of diastereomeric esters and calculation of their conformational shielding models

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Product

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Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools

Crystalline‐State Conformational Analysis of MαNP Esters, Powerful Resolution and Chiral ¹H NMR Anisotropy Tools