198:
24:
433:
775:
Reinhard Schulz; Armin
Schweig; Klaus Hartke; Joachim Koester (1983). "Theory and application of photoelectron spectroscopy. 100. Variable-temperature photoelectron spectral study of 1,3-dithiol-2-one and 4,5-disubstituted 1,3-dithiol-2-ones. Thermal generation of 1,2-dithiete, 3,4-disubstituted
567:
Jonas, V; Frenking, G (1991). "On the crucial importance of polarization functions for the calculation of molecules with third-row elements: the conformations of chlorocarbonyl isocyanate ClC(O)NCO and the equilibrium of 1,2-dithioglyoxal with its cyclic isomer 1,2-dithiete".
504:
Diehl, F.; Meyer, H.; Schweig, A.; Hess, B. A.; Fabian, J. (September 1989). "1,2-Dithiete is more stable than 1,2-dithioglyoxal as evidenced by a combined experimental and theoretical IR spectroscopic approach".
237:
710:
Donahue, JP; Holm, RH (1998). "3,4-Bis(1-adamantyl)-1,2-dithiete: the First
Structurally Characterized Dithiete Unsupported by a Ring or Benzenoid Frame".
748:
T. Shimizu; H. Murakami; Y. Kobayashi; K. Iwata; N. Kamigata (1998). "Synthesis, Structure, and Ring
Conversion of 1,2-Dithiete and Related Compounds".
803:
Mucha, M; Pagacza, M; Mielke, Z (6 June 2008). "Infrared detection of dithioglyoxal from photolysis of 1,3-dithiol-2-one in solid argon and nitrogen".
23:
405:
694:
661:
394:
423:
of 1,3-dithiol-2-one. Quantum chemical calculations reproduce the observed greater stability of 1,2-dithiete only if large basis-sets with
212:
359:
893:
888:
883:
176:
412:
in a low temperature matrix. The open ring isomer, dithioglyoxal, HC(S)C(S)H, is less stable than the 1,2-dithiete.
390:
526:
Vijay, D; Priyakumar, UD; Sastry, GN (2004). "Basis set and method dependence of the relative energies of C
401:
379:
382:
are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of
424:
409:
386:
375:
48:
677:
Drabowicz, J; Lewkowski, J; Kudelska, W; Zając, A (2008). "Four-membered Rings with Two Sulfur Atoms".
812:
610:
577:
547:
336:
36:
193:
78:
859:
400:
Unsubstituted 1,2-dithiete has been generated in thermolytic reactions and was characterized by
842:
quantum-chemical calculations of the energies and structures of 1,2-acetylenedithiol isomers".
727:
690:
657:
851:
820:
785:
757:
719:
682:
649:
618:
585:
555:
514:
265:
139:
119:
88:
197:
112:
816:
614:
581:
551:
353:
622:
877:
686:
653:
589:
389:. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a
863:
164:
824:
559:
383:
378:
that contains two adjacent sulfur atoms and two sp-hybridized carbon centers.
855:
723:
484:
420:
293:
130:
341:
731:
331:
789:
518:
151:
761:
490:
316:
352:
Except where otherwise noted, data are given for materials in their
432:
431:
118:
111:
101:
838:
Frolov, YV; Vashchenko, AV; Mal'kina, AG; Trofimov, BA (2009). "
644:
Zoller, U (1996). "Four-membered Rings with Two Sulfur Atoms".
601:
calculations on the 1,2-dithioglyoxal/1,2-dithiete isomerism".
597:
Gonzalez, L; Mo, O; Yanez, M (13 December 1996). "High-level
181:
163:
776:1,2-dithietes, and dialkyl tetrathiooxalates".
87:
8:
196:
138:
15:
778:Journal of the American Chemical Society
679:Comprehensive Heterocyclic Chemistry III
646:Comprehensive Heterocyclic Chemistry II
636:
493:- an analogue with only one sulfur atom
242:
217:
192:
406:ultraviolet photoelectron spectroscopy
395:3,4-Bis(trifluoromethyl)-1,2-dithiete
224:Key: CTGHONDBXRRMRC-UHFFFAOYSA-N
7:
743:
741:
648:. Vol. 1B. pp. 1113–1138.
419:-dithioglyoxal) by low temperature
154:
487:- the corresponding saturated ring
452:. Selected distances and angles: r
397:is a particularly stable example.
14:
681:. Vol. 2. pp. 811–852.
415:The dithione can be prepared (as
687:10.1016/B978-008044992-0.00218-2
654:10.1016/B978-008096518-5.00035-6
277:
221:InChI=1S/C2H2S2/c1-2-4-3-1/h1-2H
22:
844:Journal of Structural Chemistry
356:(at 25 °C , 100 kPa).
283:
271:
1:
623:10.1016/S0009-2614(96)01240-7
825:10.1016/j.cplett.2008.04.088
590:10.1016/0009-2614(91)90064-G
560:10.1016/j.cplett.2003.11.021
436:Structure of the dithiete S
910:
856:10.1007/s10947-009-0029-8
724:10.1107/S0108270198002935
350:
305:
258:
233:
208:
71:
59:
47:
35:
30:
21:
805:Chemical Physics Letters
603:Chemical Physics Letters
570:Chemical Physics Letters
540:Chemical Physics Letters
53:1,2-Dithiacyclobut-3-ene
712:Acta Crystallographica
473:
425:polarization functions
402:microwave spectroscopy
387:organosulfur compounds
435:
410:infrared spectroscopy
376:heterocyclic compound
49:Systematic IUPAC name
337:2,3-Dihydrothiophene
37:Preferred IUPAC name
894:Four-membered rings
889:Sulfur heterocycles
817:2008CPL...458...39M
790:10.1021/ja00352a004
615:1996CPL...263..407G
582:1991CPL...177..175J
552:2004CPL...383..192V
519:10.1021/ja00201a076
301: g·mol
18:
884:Organic disulfides
498:Additional reading
474:
391:dithiolene complex
374:is an unsaturated
360:Infobox references
306:Related compounds
66:1,2-Dithiaannulene
16:
784:(14): 4519–4528.
762:10.1021/jo9806714
756:(23): 8192–8199.
696:978-0-08-044992-0
663:978-0-08-096518-5
609:(3): 407–413(7).
513:(19): 7651–7653.
368:Chemical compound
366:
365:
324:Related compounds
177:CompTox Dashboard
120:Interactive image
113:Interactive image
64:Dithiacyclobutene
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718:(8): 1175–1178.
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546:(1–2): 192–197.
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507:J. Am. Chem. Soc
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266:Chemical formula
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464:= 2.072 Å, <
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312:Related thietes
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850:(2): 195–200.
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811:(1–3): 39–43.
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576:(2): 175–183.
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354:standard state
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194:DTXSID70221149
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478:
468:= 78.3°, <
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750:J. Org. Chem
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399:
371:
370:
72:Identifiers
60:Other names
41:1,2-Dithiete
380:Derivatives
259:Properties
878:Categories
631:References
538:isomers".
485:Dithietane
460:= 1.738, r
456:= 1.362, r
427:are used.
421:photolysis
294:Molar mass
131:ChemSpider
100:3D model (
79:CAS Number
840:Ab initio
599:ab initio
342:Thiophene
89:7092-01-5
17:Dithiete
864:93780466
479:See also
384:aromatic
372:Dithiete
332:Thiirene
62:Dithiete
813:Bibcode
732:9760719
611:Bibcode
578:Bibcode
548:Bibcode
472:= 102°.
250:S1SC=C1
152:PubChem
862:
730:
693:
660:
491:Thiete
317:Thiete
245:c1css1
238:SMILES
165:138918
140:122516
31:Names
860:S2CID
470:S-C-S
466:S-S-C
417:trans
299:90.16
213:InChI
102:JSmol
728:PMID
691:ISBN
658:ISBN
408:and
852:doi
821:doi
809:458
786:doi
782:105
758:doi
720:doi
716:C54
683:doi
650:doi
619:doi
607:263
586:doi
574:177
556:doi
544:383
515:doi
511:111
462:S-S
458:C-S
454:C=C
448:Me)
444:(CO
182:EPA
155:CID
880::
858:.
848:50
846:.
819:.
807:.
780:.
754:63
752:.
740:^
726:.
714:.
689:.
656:.
617:.
605:.
584:.
572:.
554:.
542:.
509:.
404:,
393:.
866:.
854::
827:.
823::
815::
792:.
788::
764:.
760::
734:.
722::
699:.
685::
666:.
652::
625:.
621::
613::
592:.
588::
580::
562:.
558::
550::
536:2
534:H
532:2
530:S
528:2
521:.
517::
450:2
446:2
442:2
440:C
438:2
287:2
284:S
281:2
278:H
275:2
272:C
184:)
180:(
104:)
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