Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap

Grethe Rindorf; Flemming S. Jorgensen; James P. Snyder

doi:10.1021/jo01314a027

Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap

Grethe Rindorf, Flemming S. Jorgensen, James P. Snyder

18 Citations (Scopus)

Abstract

The crystal and molecular structure of di-tert-adamantyl disulfide (1, DAD; C20H30S2) has been determined from diffractometer data. The unit cell is monoclinic: space group P21/c; a = 12.015 (3), b = 11.556 (3), c = 12.959 (3) Å; β = 90.42 (2)°; V = 1799 Å3; Z = 4; = 1.24 Mg/m-3. Least-squares refinements gave R = 0.074 for 649 observed reflections. The torsion angle θ(CSSC) = 110.5 (9)°. The observation of an enlarged S-S dihedral angle permits a tentative extension of the correlation between 0(CSSC) and the photoelectron spectroscopically determined ionization energy difference, ∆E(n+-n-), and disulfide torsional angles above 90°. The molecular geometry of t-Bu-SS-t-Bu is revised accordingly.

Original language	English
Journal	Journal of Organic Chemistry
Volume	45
Issue number	26
Pages (from-to)	5343-5347
Number of pages	5
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo01314a027
Publication status	Published - 1 Jan 1980

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Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap. / Rindorf, Grethe; Jorgensen, Flemming S.; Snyder, James P.

In: Journal of Organic Chemistry, Vol. 45, No. 26, 01.01.1980, p. 5343-5347.

Research output: Contribution to journal › Journal article › Research › peer-review

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title = "Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap",

abstract = "The crystal and molecular structure of di-tert-adamantyl disulfide (1, DAD; C20H30S2) has been determined from diffractometer data. The unit cell is monoclinic: space group P21/c; a = 12.015 (3), b = 11.556 (3), c = 12.959 (3) {\AA}; β = 90.42 (2)°; V = 1799 {\AA}3; Z = 4; = 1.24 Mg/m-3. Least-squares refinements gave R = 0.074 for 649 observed reflections. The torsion angle θ(CSSC) = 110.5 (9)°. The observation of an enlarged S-S dihedral angle permits a tentative extension of the correlation between 0(CSSC) and the photoelectron spectroscopically determined ionization energy difference, ∆E(n+-n-), and disulfide torsional angles above 90°. The molecular geometry of t-Bu-SS-t-Bu is revised accordingly.",

author = "Grethe Rindorf and Jorgensen, {Flemming S.} and Snyder, {James P.}",

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T1 - Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap

AU - Rindorf, Grethe

AU - Jorgensen, Flemming S.

AU - Snyder, James P.

PY - 1980/1/1

Y1 - 1980/1/1

N2 - The crystal and molecular structure of di-tert-adamantyl disulfide (1, DAD; C20H30S2) has been determined from diffractometer data. The unit cell is monoclinic: space group P21/c; a = 12.015 (3), b = 11.556 (3), c = 12.959 (3) Å; β = 90.42 (2)°; V = 1799 Å3; Z = 4; = 1.24 Mg/m-3. Least-squares refinements gave R = 0.074 for 649 observed reflections. The torsion angle θ(CSSC) = 110.5 (9)°. The observation of an enlarged S-S dihedral angle permits a tentative extension of the correlation between 0(CSSC) and the photoelectron spectroscopically determined ionization energy difference, ∆E(n+-n-), and disulfide torsional angles above 90°. The molecular geometry of t-Bu-SS-t-Bu is revised accordingly.

AB - The crystal and molecular structure of di-tert-adamantyl disulfide (1, DAD; C20H30S2) has been determined from diffractometer data. The unit cell is monoclinic: space group P21/c; a = 12.015 (3), b = 11.556 (3), c = 12.959 (3) Å; β = 90.42 (2)°; V = 1799 Å3; Z = 4; = 1.24 Mg/m-3. Least-squares refinements gave R = 0.074 for 649 observed reflections. The torsion angle θ(CSSC) = 110.5 (9)°. The observation of an enlarged S-S dihedral angle permits a tentative extension of the correlation between 0(CSSC) and the photoelectron spectroscopically determined ionization energy difference, ∆E(n+-n-), and disulfide torsional angles above 90°. The molecular geometry of t-Bu-SS-t-Bu is revised accordingly.

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U2 - 10.1021/jo01314a027

DO - 10.1021/jo01314a027

M3 - Journal article

AN - SCOPUS:0006032229

SN - 0022-3263

VL - 45

SP - 5343

EP - 5347

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

Crystal and Molecular Structure of Di- tert-adamantyl Disulfide. Extension of the Correlation between the Sulfur-Sulfur Dihedral Angle and the Sulfur Lone-Pair Energy Gap

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