Supporting Information For: Heterogeneous Oxidation of Catechol. DOI: /acs.jpca.5b Publication Date (Web): September 25, 2015
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1 Supporting Informtion For: Heterogeneous Oxidtion of Ctechol DOI: /cs.jpc Puliction Dte (We): Septemer 25, 2015 Elizeth A. Pillr, Ruixin Zhou, nd Mrcelo I. Guzmn* Deprtment of Chemistry, University of Kentucky, Lexington, Kentucky 40506, Unites Sttes *Corresponding uthor s emil: mrcelo.guzmn@uky.edu The Journl of Physicl Chemistry A Content Tles Tle S1 Tle S2 Tle S3 Tle S4 Tle S5 Tle S6 Tle S7 Tle S8 Tle S9 References Pges S2 S3 S4 S5 S6 S7 S8 S9 S10 S11 S1
2 Tle S1. Virtionl ssignment for ctechol film Wvenumer (cm -1 ) Intensity Assignment 3450 s ν(o-h) 3323 s ν(o-h) 3051 m ν(c-h) 1618, 1595 m, m ν(c=c) 1512 s ν(c=c) 1471 s ν(c=c) 1363 s ν(c=c) 1255 s δ(c-h) 1190 s δ(o-h) 1095 s δ(c-h) 1041 s δ(c-h) 918 w ρ(c-h) 849 m ρ(c-h) 769 s ν(c=c) 741 s ρ(c-h) w = wek; m = medium; s = strong. All ssignments re sed on theoreticl nd experimentl studies. 1 S2
3 Tle S2. Virtionl ssignments for oxidized film Wvenumer (cm -1 ) Intensity Assignment 3393 m ν(o-h) w, ν(o-h) 1737 sh ν(c=o) 1694 sh ν(c=o) 1679 s ν(c=o) 1632 w ν(c=c) 1594 s ν(c=c) 1520 w ν(c=c) 1408 m δ(c=c) 1355,1315 m, m δ(c=c-h) 1262, 1197 s, s ν(c-o) 1216 w δ(c=c-h) 1118 w ν(c-o) 835 m ρ(c=c-h) w = wek; m = medium; s = strong; sh = shoulder; = rod. S3
4 Tle S3. Virtionl ssignment of cis,cis-muconic cid Wvenumer (cm -1 ) Intensity Assignment m, r ν(o-h) 1680 s ν(c=o) 1635 sh ν(c=c) 1591 s ν(c=c) 1408 m δ(c=c) 1355,1316 m, m δ(c=c-h) 1258, 1197 s, s ν(c-o) 914 w ρ(o-h) w = wek; m = medium; s = strong; sh = shoulder; r = rod. Assignments sed on experimentl results. 2 S4
5 Tle S4. Virtionl ssignment of mleic cid Wvenumer (cm -1 ) Intensity Assignment 3059 m ν(c-h) m, ν(o-h) 1708 s ν(c=o) 1637 w ν(c=c) 1579 s ν(c=c) 1461 m δ(c-o-h) 1436 m δ(c=c-h) 1264 s ν(c-o) 1221 m δ(c=c-h) 950 w ν(c=c) 871 m ρ(c-h) w = wek; m = medium; s = strong; = rod. Assignments sed on experimentl nd theoreticl results. 3 S5
6 Tle S5. Virtionl ssignment of glyoxylic cid. Wvenumer (cm -1 ) Intensity Assignment vs, r ν(o-h) 1727 vs ν(c=o) 1630 m νs(o-c-o) 1231 s ν(c-o) + δ(o-h) 1087, 1043 s, vs δ(c-c-h) w = wek; m = medium; s = strong; r = rod. Assignments sed on experimentl results. 4 S6
7 Tle S6. Virtionl ssignment of oxlic cid Wvenumer (cm -1 ) Intensity Assignment 3458 vs ν(o-h) 1684 vs νs(o-c-o) 1251 vs νs(c-o) + δ(o-c-o) 1133 m ν(c-oh) 725 s δ(o-c-o) w = wek; m = medium; s = strong. Assignments sed on experimentl results. 4 S7
8 Tle S7. Virtionl ssignment of 1,2,3-trihydroxyenzene Wvenumer (cm -1 ) Intensity Assignment 3375 s ν(o-h) 3245 s ν(o-h) 3056 w ν(c-h) 1633 sh ν(c=c) 1622 s ν(c=c) 1525 s ν(c=c) 1488 s δ(c-o-h) 1363 s δ(o-h) 1290 s δ(c-o-h) 1243 s δ(c-h) 1190 s δ(c=c-h) 1061 m ν(c=c) 1004 s ρ (C=C-H) 847 w ρ (C=C-H) 830 w ρ(c=c-o) 764 m ν(c=c) 805 s ρ(=c-o-h) w = wek; m = medium; s = strong; sh = shoulder. Assignments sed on experimentl nd theoreticl results. 5 S8
9 Tle S8. Virtionl ssignment of 1,2,4-trihydroxyenzene Wvenumer (cm -1 ) Intensity Assignment 3256 s ν(o-h) 1622 m ν(c=c) 1577 sh ν(c=c) 1514 sh ν(c=c) 1386 s δ(o-h) 1300 s δ(c-o-h) 839 m δ(c-o-h) 790 s ρ(c-h) w = wek; m = medium; s = strong; sh = shoulder. Assignments sed on experimentl nd theoreticl results. 6 S9
10 Tle S9. Pseudo-first order rte constnts (k) nd ssocited stndrd devitions (s) for the decy of ctechol nd production of cis,cis-muconic cid t vrile RH extrcted from the equtions [ctechol] = [ctechol] 0 + e k ctechol+o3 t nd [cis,cis-muconic cid]/ [cis,cis-muconic cid] inf = (1 e -k cis,cis-muconic cid t ). RH (%) k ctechol+o3 (s -1 ) k cis,cis-muconic cid (s -1 ) S10
11 References (1) Rmirez, F. J.; Nvrrete, J. T. L. Norml Coordinte nd Rottionl Brrier Clcultions on 1,2-dihydroxyenzene. Virtionl Spectroscopy 1993, 4, (2) Sǒhár, P.; Vrsányi, G. Y. An IR spectroscopic study of muconte isomers. J. Mol. Struct. 1968, 1, (3) Mçôs, E. M. S.; Fusto, R.; Lundell, J.; Pettersson, M.; Khrichtchev, L.; Räsänen, M. A Mtrix Isoltion Spectroscopic nd Quntum Chemicl Study of Fumric nd Mleic Acid. J. Phys. Chem. A 2001, 105, (4) Niculescu, M.; Ledeţi, I.; Bîrzescu, M. New methods to otin croxylic cids y oxidtion rections of 1,2-ethnediol with metllic nitrtes. J. Orgnomet. Chem. 2014, 767, (5) Mustf, C. Virtionl Spectroscopy of Pyrogllol with glnce on the prolems of formtion of Dimer. Reserch Journl of Chemistry nd Environment 2013, 17, (6) Etiw, S. E. H.; Werid, A. H. Three-dimensionl orgnotin hexcynoferrte polymers s effective oxidizing regents towrds phenols. Appl. Orgnomet. Chem. 2010, 24, S11
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