Synthesis, characterization and crystal structures of 1,7-dioxa-4-thia-10-azacyclododecane ([12]aneNO2S) and [HG([12]aneNO2S)(NO3)2]

Byriel K.A., Gahan L.R., Kennard C.H.L. and Sunderland C.J. (1993) Synthesis, characterization and crystal structures of 1,7-dioxa-4-thia-10-azacyclododecane ([12]aneNO2S) and [HG([12]aneNO2S)(NO3)2]. Journal of the Chemical Society, Dalton Transactions, 4: 625-629. doi:10.1039/DT9930000625


Author Byriel K.A.
Gahan L.R.
Kennard C.H.L.
Sunderland C.J.
Title Synthesis, characterization and crystal structures of 1,7-dioxa-4-thia-10-azacyclododecane ([12]aneNO2S) and [HG([12]aneNO2S)(NO3)2]
Journal name Journal of the Chemical Society, Dalton Transactions
ISSN 1472-7773
Publication date 1993-01-01
Sub-type Article (original research)
DOI 10.1039/DT9930000625
Issue 4
Start page 625
End page 629
Total pages 5
Language eng
Subject 1600 Chemistry
Abstract Reaction of 6-(4-methylphenylsulfonyl)-1,11-bis(4-methylphenylsulfonyloxy)-3,9-dioxa-6- azaundecane and ethane-1,2-dithiol in the presence of NaH, results after removal of the protecting group, in the unexpected isolation of the twelve-membered macrocycle 1,7-dioxa-4-thia-10-azacyclododecane,[12]aneNOS. The product, suggested to arise from the intramolecular displacement of a tosyl group by a thioether instead of the terminal thiol as in the expected ring closing procedure, was characterised by C NMR spectroscopy, mass spectrometry, microanalysis and a single-crystal X-ray structure determination. The macrocycle crystallizes in the monoclinic space group P2, with a = 7.448(5), b = 5.1740(10), c = 12.769(9) Å, β = 93.28(2)°, Z = 2 with R = 0.046. All the donors in the macrocyclic ring are in the endodentate conformation with close contacts between the N-H and atoms O(1) and O(7). Reaction of mercury nitrate with 1 molar equivalent of [12]aneNOS in methanol, and subsequent crystallization of the product, resulted in colourless prisms of [Hg([12]aneNOS)(NO)] which crystallize in the monoclinic space group P2/c, with a = 9.165(17), b = 10.657(15), c = 14.80(2) Å, β = 92.57(8)°, Z = 4 with R = 0.055. In this molecule the mercury(II) cation is co-ordinated by the macrocyclic donors and the nitrate anions, one in a bidentate manner, the other in a monodentate mode.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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