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Inter- and intra-molecular hydrogen bonding in bis(2-amino-5-fluoro-3-methylphenyl)disulfide

Inter- and intra-molecular hydrogen bonding in bis(2-amino-5-fluoro-3-methylphenyl)disulfide
Inter- and intra-molecular hydrogen bonding in bis(2-amino-5-fluoro-3-methylphenyl)disulfide
Bis(2-amino-5-fluoro-3-methylphenyl)disulfide was obtained by oxidation of 2-amino-5-fluoro-3-methylbenzenethiol and was characterized by elemental analysis, IR and 1H-NMR spectroscopy. The X-ray structure was determined. Crystal data: C14H14N2F2S2: Monoclinic, P21 /n, a = 11.8268(3), b = 9.5770(3), c = 12.3977(3) Å, ? = 98.079(2)°, V = 1390.29(7) Å, Z = 4. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds. Index Abstract Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide J. E. Drake1, M. B. Hursthouse2, M. E. Light2, R. Maheshwari3, K.G. Ojha3, R. Ratnani3* Bis(2-amino-5-fluoro-3-methylphenyl)disulfide is linked into a three-dimensional frame work by a combination of intermolecular N–H···F and N–H···N and intramolecular N–H···S hydrogen bonds. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.
4-benzothiazines, ketones, conversion, crystal, 2, rearrangement, disulfide, 4h-1, 2'-dithiodianiline, synthesis, structure, hydrogen bonding
1074-1542
553-556
Drake, J. E.
dee0cd4d-79bf-4024-ad9c-d61bfaf9216b
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Maheshwari, R.
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Ojha, K. G.
d1e826f2-9fd5-4734-8d4b-475986e11dff
Ratnani, R.
5c33e340-5b43-4fae-b43d-c37ae26100ff
Drake, J. E.
dee0cd4d-79bf-4024-ad9c-d61bfaf9216b
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Maheshwari, R.
ec4b0295-c7e1-4cb8-a09b-c73e6b44ead4
Ojha, K. G.
d1e826f2-9fd5-4734-8d4b-475986e11dff
Ratnani, R.
5c33e340-5b43-4fae-b43d-c37ae26100ff

Drake, J. E., Hursthouse, M. B., Light, M. E., Maheshwari, R., Ojha, K. G. and Ratnani, R. (2008) Inter- and intra-molecular hydrogen bonding in bis(2-amino-5-fluoro-3-methylphenyl)disulfide. Journal of Chemical Crystallography, 38 (7), 553-556. (doi:10.1007/s10870-008-9353-7).

Record type: Article

Abstract

Bis(2-amino-5-fluoro-3-methylphenyl)disulfide was obtained by oxidation of 2-amino-5-fluoro-3-methylbenzenethiol and was characterized by elemental analysis, IR and 1H-NMR spectroscopy. The X-ray structure was determined. Crystal data: C14H14N2F2S2: Monoclinic, P21 /n, a = 11.8268(3), b = 9.5770(3), c = 12.3977(3) Å, ? = 98.079(2)°, V = 1390.29(7) Å, Z = 4. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds. Index Abstract Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide J. E. Drake1, M. B. Hursthouse2, M. E. Light2, R. Maheshwari3, K.G. Ojha3, R. Ratnani3* Bis(2-amino-5-fluoro-3-methylphenyl)disulfide is linked into a three-dimensional frame work by a combination of intermolecular N–H···F and N–H···N and intramolecular N–H···S hydrogen bonds. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.

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Published date: July 2008
Keywords: 4-benzothiazines, ketones, conversion, crystal, 2, rearrangement, disulfide, 4h-1, 2'-dithiodianiline, synthesis, structure, hydrogen bonding

Identifiers

Local EPrints ID: 54444
URI: http://eprints.soton.ac.uk/id/eprint/54444
ISSN: 1074-1542
PURE UUID: ea12bd2d-4c5e-424e-8336-974e4386f76b
ORCID for M. E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 05 Aug 2008
Last modified: 20 Jul 2019 01:10

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Contributors

Author: J. E. Drake
Author: M. E. Light ORCID iD
Author: R. Maheshwari
Author: K. G. Ojha
Author: R. Ratnani

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