2010
DOI: 10.1016/j.jorganchem.2010.01.029
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New morpholine- and piperazine-functionalized triphenylantimony(V) catecholates: The spectroscopic and electrochemical studies

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Cited by 50 publications
(18 citation statements)
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“…Scheme 2 represents the spatial configuration of piperazine substituent as a result of molecular modeling (''HyperChem'' 8.0.3). It is in agreement with structural results which are known for the catecholate dianion of this o-quinone [8]. It becomes clear that four protons (H⁄) can effectively interact with orbital occupied by unpaired electron which is p à in character.…”
Section: Resultssupporting
confidence: 90%
“…Scheme 2 represents the spatial configuration of piperazine substituent as a result of molecular modeling (''HyperChem'' 8.0.3). It is in agreement with structural results which are known for the catecholate dianion of this o-quinone [8]. It becomes clear that four protons (H⁄) can effectively interact with orbital occupied by unpaired electron which is p à in character.…”
Section: Resultssupporting
confidence: 90%
“…The presence of electron-withdrawing nitro group in 6 promotes the anodic oxidation potential shift and reduces the stability of the monocationic derivative of complex. (15) 119.74 (13) 87.46 (6) 87.17(6) O(1)eSb(1)eC (22) 84.68 (13) 120.66 (6) 120.73(6) O(1)eSb(1)eC (29) 126.18 (13) 118.40 (6) 118.95(6) C(22)eSb(1)eC (29) 100.98 (15) 118.61 (6) 118.00(6) C(22)eSb(1)eC (15) 101.87 (15) 99.23 (6) 99.42(6) C(15)eSb(1)eC (29) 111.36 (15) 98.55 (7) 98.69(6) O(2)eSb(1)eC (22) 161.64 (13) 86.98 (6) 87.19(6) O(2)eSb(1)eC (15) 90.79 (13) 166.65 (6) 166.23(5) O(2)eSb(1)eC (29) 86.42 (13) 88.65 (6) 88.66(6) 3 3 0.95 0.70 1 1.43 (4-Cl-3,6-DBCat)Sb(p-Cl-Ph) 3 4 0.97 0.71 n > 1 1.46 (6-NO 2 -3,5-DBCat)Sb(o-Tol) 3 6 1.20 0.55 n > 1 1.63 (6-Cl-3,5-DBCat)Sb(p-Tol) 3 7 1.00 0.72 1 1.58 (6-Br-3,5-DBCat)Sb(p-Tol) 3 8 0.99 0.82 1 1.45 (3,6-DBCat)SbPh 3 [14] e 0.89 0.82 1 1.40 (4-Cl-3,6-DBCat)SbPh 3 [12] e 0.98 0.81 1 1.37 (6-Cl-3,5-DBCat)SbPh 3 [12] e 1.00 0.52 1 1.60…”
Section: Electrochemical Investigationsmentioning
confidence: 99%
“…1 H NMR (CDCl 3 , ppm): 1.40 (s, 9H, t-Bu), 1.39 (t, 3 J(H,H) ¼ 7.8 Hz, 9H, 3 CH 2 CH 3 ), 1.57 (s, 9H, t-Bu), 1.89 (q, 3 J(H,H) ¼ 7.8 Hz, 6H, 3 CH 2 CH 3 ), 6.575 (s, 1H, C 6 H 1 ). 13 Triarylantimony(V) catecholates 2e8 were synthesized from the corresponding o-benzoquinones and triarylstibines in toluene solution as described previously [8,9,12,13,16,25,26]. The yields of aimed products were more 85%.…”
Section: Synthesesmentioning
confidence: 99%
“…But in this case, we have no found the formation of spiroendoperoxides as described in refs. [6,30]. The reaction of bis-catecholate 1 with air oxygen leads to loss of one trimethylantimony group forming cherry-red colored quinone-catecholate (Me 3 Sb(Cat-Q)) (3) (Scheme 3).…”
Section: Resultsmentioning
confidence: 99%