Medhi, K C

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/ndion J, Phya. 5 lA , 399-413 (1977)The vibrational spectra of 2-, 3-and 4-acetylpyridineK. C. MedhiDepartment of Physics, Qauhati University, QauhatiAA (Received ](> September 1976)111 infrared absorption s}K>etra in the ro^ i^on 4000—60^ 111"^  and the laser Raman spectra in pure liquid state Ixave been studied for 2-, 3- and 4-acetylpyi*idine. An (essent ially complete assignment, of the (»bserved frequencies is givcMi.1 I ntro nucrtoNIn extension of tlie earlier study of tlu^  vibrational spectra of some substitut ed pyridines (MedJii ik MukUerjee 1905, Medhi 19t)5, 1972), t-h(^  infrared and Raman spectra of 2-, 3- and 4- acetylpyridim  ^ liave been investigated in the pure liquid state. A few characteristic infrared bands were repoi ted by Katritzky & Gardner (1958), Katritzky & Hands (1958) and Katritzky et al (1958) togetlu*r with their assignments in the ease of the three isonuus of acetyljiyridine in solution in cliloroform, and by Hideyo Shindo (1957) in thc^  case of 2-acotylpyridine. There appears to bo no previous report on the Raman spectra of those molecules.The prestuit paper deals with a detailed st udy ol the infrared and Raman spectra of th(^  three isomeric acetylpyridincs. An (essentially complete assign- meat of the observed vibrational frequenciex, based on the state ol pola-iization of the Raman linos and comparison with the assignmemts proposed lor the l elated molecules (Green el al 1963, Spinner 1963, Long & Georges 1903, Berezin &■ Klkiii 1973, Mross & Zundel 1970), is presented.2. E xperimentalThe compounds used in this work were obtained from Koch-Light Labora­tories Ltd., England. The samples were purified by fractional distillation, and in each case the proper fraction distilled at a constant temperature was collected for use in the experiment!.The infrared absorption spectra in the region 4000—400 cm“  ^ were recorded on a Becltman IR-12 spectrophotometer. The calibration of the instrument was checked by the spectrum of a polystyrene film. The far infrared spectra in the range 500-50 cm”  ^wore scanned in the pure liquid state using a Perkin-Elmer Model 180 spectrophotometer and a 0.1 mm polyethylene ceU. The Raman spectra were taken on a Cary Model 82 laser Raman spectrophotometer and a Spex RamacompyO. The spectra were excited by either the 4880A (60 mW) or 6145A (300 mW) line of an argon ion laser. The polarization of the Raman lines was399400 K. C. Medhimeasui-t^ d for two different mutually perpendicular orientations of the analyser in the scattered bc^ am, while the piano of polarization of the laser beam was kept fixed.3. R esults akd DiscussionTlie observed infrared frequencies and Raman shifts of the three compounds togc^ t-lxfu' with their approximatci intonsitios and assignments are listed in table J-3. For ciunjiarison th(^  iundaim^ntal frequencies of pyridine (WilmshurstTable I. \Tibrationa] fro(|uencics and assignments for 2-acetylpjTidineInfrttrod Kaman (ern- )^ Aflsignmoiit160 (w) 163 (2) dp a" fundam(3ntal2 1 fi (w) fuudameniah— C-OH3 Out-of piano deformation: m  (w) 360 (1) p a' fimdainonlal:m)5 (sh) a' fundamental,— fJ-CHs in-piano deformation ^ioe (w) a" and a'' fundamentals,— C““0 out-of.plane deformation482 v^w) 492 (0) a"' fundamental/51)0 (VH) ri90 (0 ) p a' and a' fundamentala, ^  — C “  0 in -plaixe deformationr. 2 2  (rn) 622 (2 ) p a' fundamental700 (w) a" fundamental740 (H) 760 (3) p a' fundamental779 {vti) -- 783 (0) ii," fundamental903 (W) a"' fundamental963 (l)p a' fundamental,— OHJ in-plane rooking9M (h) a'^  fundamental990 {h) 995 (10) p a' fundamental10 18 (m) fundamental / . — CHs out-of-plane rocking //"1043 {a) 1044 (5) p a' fundamental1080 (ml 1086 (1 ) T» a' fundamental1 1 0 0  (\ri9) 1 1 0 1  (l)p a' fundamental1 140 (m) 1150 (0 )p a' fundamoiital1238 (vh) 1238 (2) p a' fundamental^— O-OHs stretchingVibrational spectra of 2-, 3-and 4-acetylpyridineT a b lo  1 (o o n td .)401Infrared (cm*^) Kam an (cm-’ ) Assignment1281 (vh) 1282 (2) p a' fimdamontal1296 (VB) 1296 (2) p a^  fundamental1357 (v«) a" fundamental.— fJHa symmetric dcfonnal ion1421 (s) a" fundaniontal1437 (vs) 1437 (2) p and a" fundamentals,— OHti Bsyinmetnc defnrmat loii1465 (r) a' fundamental1560 (m) 2X779==. 1668 (A')1568 (h) 1669 (1) p a " Fiuid ai i lontal1685 (vb) 1686 (6) p a' Fundamental1616 (w) 622+996==-1618 (A')1659 (W) 622 + 1043 =  1665 (A')1702 (vH) 1097 (5) p a' fimdamental,— 0 = 0  stretohinp ^1826 (vw) 59041238---'1828 (A')1870 (W) 690 + 12 8 1 -  1871 (A41005 (w) 2 x 9 6 4 -  1908 (A')1969 (w) 964 1-1018= 1972 (A')2107 (vw) 964 -1 1146 = 2 10 0  (A'")2190 (vw) 964 + 1238 =  2192 (A^)22a8 (vw) 954 4  1281= 2236  (A^)2309 (W) 740 ] 1668 =  2308 (A')2369 (vw) 779 +  1586= 2364 (A^)2444 (vw) 740 +  1702 =  2442 (A')2480 (vw) 779 +  1702 =  2481 (A'^ )2518 (vw) 1238 + 12 81= 2619  (A')2637 (w) 1100 +  1437 =  2637 (A' or A")2684 (vW) 996 +  1585 =  2681 (A')2663 (w) 1296 +  1357 =  2663 (A')2670 (w) 2700 ^vw)1100 +  15 0 8* 26 6 8  (A'+1 2 8 1 x 1 4 2 1  =  2702 (A')2768 (vw) 1 2 9 6 f  1466 =  2761 (A')402 K . C. M edhiTable 1 (coatd.)lufrfii'od Biaman (cni"^) Assignment2810 (w) 1238 +  1586:=2823 (A')2804 w^) 2X1437-.2874 (A')2926(m) 2924 (2) p a' and o,'* fundamentals,— 0H3 symmetric stretching2982 (Bh) \ aOll ( m ) / 3010 (1) p a' and a'' fundamentals,— OHfl asymmetric stretching:i000 (m) 3062 (2) i» a', a', a' and a' fundamentals3130 (m) 3138 (0) p 2x1568-=3130 (A')3106 (w) 3168 (0 p 2x1586 =  3170 (A')2388 (w) 2x1702 =  3404 (A')(H)^Hfcrong ; (in)=:medium ; (w) - Woak ; (v)= v o r y  ; (sh) “ shoulcier ;]):=;= polarizocl ; dp = dopolarizod.M 2. Vibrational fioquoncioK and aBflignmentB for 3-acetylpyridineInfrarod (om“ )^ Haman (crn-^) Assignment102 (w) 164 (J) dp a*' fundamental221 (w) a"' fundamental— O-OHs out-of-plane deformation306 (w) 168 (0) p a" fundamental383 (W) a" fundamental,— O-CHq ill-plane deformation405 (w) a"^  and b," fundamontals,— C =0 out-of-plane deformation472 (w) a" fundamental500 ( v h ) 691 (0) p a" and a' fundamentals,— C-—0 in plane deformation023 (h) 624 (1 ) p a' fundamental704 (vs) a"' fundamental749 (m) 751 (2) p a' fundamental809 (va) a*" fundamental928 (w) a ' fundamental957 (0) p a' fundamontab— OHp in-plane rocking958 (vs) a^  fundamentalV i b r a t i o n a l  s p e c t r a  o f  2 - , ^ - a n d  4 b - a c e t y l p y r i d i n eT a b le  2  ( c o n td ) .In frared  (em -^) K aniun  (em** )^ A BBi gmnoiit.1023 (\=h) ii/' liindiiiiio iital,— OH3  oui-of-idtuio ruekingJ 034  (nil) 1035 (10) j3 fundtunuxilalHkS] (sli) 1078  (0) i> a' I'lmdainonLalU»J)3 (s) 1091 (Bh) a.' fuudamiuxial1 1 1 8  (s  i a' fiiudam oid alU 27 (jn) a' fiindm nonl a.lJlOr, (s; 1 105 ( 1 ) a/ Cundaiuental,— 0 -0 H ;3 strotclring1242 (h) 1243 (0 ) p a.' fu iidam eulaJ1274 (vs) 1272 ( 1 ) a' fim dam ental1325  (Hh) 023 +  704-^ 1327  (A")1 1 0 2  ( v s ) a' rundanim iial,— OH3  Kym m olne iliOorniulion1420 (vs) 1417  (0 ) a/ Umclam<>nta.11470 (Jii) a' and n" riuidain(‘-ntalB,— OU 3  ijsym m etric  dorurjiailioiJ4 78  (in) 1480  (0 ) a' (undamontaJir>7‘i ( s ) 1574 (sh) a' rim dam cnla J15S7 (vs) 1580 (3) |) a^  fundatiMmlal1 0 2 0  {w') 590 +  1 0 3 4 -  1024 (A^1053  (v') 7l»4 +  9 5 8 - - 1 0 0 2  (A')If> 0 0 1 0 8 0  (3 ) a' I'undaimmtaJ,— C —1 > Bl-rotchiri g1770 (v\') 5 9 0 +  i l9 5 r - .  17851801 {^v) 5 9 0 ^ -12 7 4 -; 1804  (A')J 025 (vv) 8 0 0 H -1118 --19 2 7  (A'O19 52  (W) 590-1 1102.^ 1952 (A')2 0 2 1  (\v) 7 4 9 +  1274---2023 (A')2 J 1 1  (vw) 749 +  1302--=2111 (A')2229  (vW) 809 +  14 20 . 2229 (A ")2o25 (v\V) 9 5 8 + 1 3 0 2 - - 2320 (A '^)2389  (vw) 2 x 1 1 9 5 .-“-2 3 9 0  ^A')2441 (vw) 9 5 8 +  1478== 2430 (A")403404T a b le  2 (co n td ).K. C. MedhiInfrared (cm-^) Bam aa ABsignment2fil3 (vw) 1093 + 1420^2613 (A')2643 (vw) 2x1274=^2548 (A')2605 (vw) 1242 h i362^:2604 (A^2645 (vw) 958 + 1690 = 2648 (a )^2856 (w) 1274+1587 = 2861 (A')2i^ 2rj (m) 2921 (2) p n' fimdamontal^— CH3 symmetric stretching29V2 (m) 3011 (in)2968 (0)  ^3006 (0) Jii' ami a" fundamentals,— CH3 asymmetric stretching3053 (m) a' fundamental3069 (2) p ix' and a' fundamentals3089 (ni) 3089 (8h) a' fundamental3168 (w) 2)sl587 =3174 (A^3367 (m) 2x1690 = 3380 (A^Table 3. Vibrational frequencies and aHHignnxontR for 4-acetylpyridinearod (cjii'^) Jturnau (cin~ )^ Assignment168 (w) 160 ( 1 ) dp a" fundamental219 (w) a." fundamental,— C-CH3  out-of-plane deformation358 (w) 364 (1) p a' fundamental417 (w) and fundamentals,^^C= 0  out-of-plane deformation405 (vw) a'' fundainontal590 (va) 589 (0) p a' and a' fundamentalB,— 0 = 0  in-piano deformation601 (vs) 603 (0) a" fundamental664 (w) 6 6 6  (2 ) dp a'^  fundamental736 (w) 739 (3) p a' fundamental817 (vs) a" fundamental875 (w) a'' fundamental962 (1) p fundamental,— CHa in-pLane rookingVibrationalIn frared  (om-^)T a b le  3 (o o n td ,)spectra o f 2-, 4^-acetylpyridine 405R am an (cm'”^ ) Aaeignxnent963 (a) fundam ental993 (a) 993 (10) p a' fundam ental1 0 2 1  (m) a" fundam ental,— CHg out-of-plano rocking1003 (b) 1064  (1) p q/ fundam ental1083 (m) 1084 (3) p a>" fundam ental1 1 1 5  (w) a' fundam ental1 2 2 0  (m) 1214  (2) p a' fundam ental1263 (b) a.' fundam ental,— C-CHa stretching1267 (vs) 1267 (2) p a' fundam ental1324  (m) 1324 (0 ) a' fundam ental1362 (vs) a' fundam ental,-“ CHa Byrnmotrio deform ation1410  (vs) a' fundam ental1423 (8 h) a/ and a" fundam onials,CHa asym m etric deformation1494 (m) 1492 ( 1 ) p a' fundam ental1657 (6 ) 1656 (0 ) a' fundam ental1597 (in) 1596 (2 ) p a' fundam ental1627 (w) 6 0 1+  1 0 2 1  ==1622 (A'^ >1666 (m) 5 9 0 + 10 6 3  =  1653 (A')1696 (vb) 1694  (3) p a' fundam ental, -C =  0  stretching1774 (sh) 817 -1-963= 1780  (A')1854 (w) 5 9 0 + 1 2 6 7 = 1 8 5 7  (A')1949 (w) 590 + 1 3 6 2 = 19 5 2  (A')2 0 0 1  (w) 5 9 0 + 1 4 1 0 = 2 0 0 0  (A')2097 (vw) 601 1-1494= 2095  (A^)2149  (vw) 590 +  1567 =  2147  (A')2177  (vw) 8 1 7 + 1 3 6 2 = 2 1 7 9  (A"^ )2209 (vw) 993 +  12 2 0 = 2 2 13  (A')2315  (w) 817 +  14 9 4 = 2 3 1 1  (A^)2386 (w) 1021 +  13 6 2 = 2 8 8 3  (A*")40« K . C. M edhiTable 3 (contd.)frared (cm“ liarnan (eiir )^ A.MsignuKiit24<I5 1085 1 1 5 5 2 - 2 4 4 5  (A )^2527 fvw) 2 1 2 5 7 - 2 5 5 1  (A )258.5 (vw) 1257 ; 1521-- 25!) 1 (A')2525 v^^ )^ 1257 ; 1552 252!) (A')2555 (vv) 1055 [ 1507-- 2550 (A )^2707 (vw) 1220 ; 1 1!)1 271 1 (A')275!) (vw) 1110   ^ 1 5 5 2 - 2 7 7 2  (A )2800 (w) 1257 ' 15!)7 2851 {A')28S7 (w) 1524 i 1 5 5 7 - 2 8 8 1  (A')2!)23 (m) 2022 (2) f) i\.' fuiulanmnlnl,- t 'Hj syjnmnlnc* si icIcliinL!,2072 (w) 2072 ( 0 ) p a' fiiml 0111 out 111.- C^Ha asynmu'l rir* si i '4 chin!2087 (m>) 1125 ; 1557 2!)S0 (A' or A'':)0t)!l (nO 5010 (sh) n" I'nni.hnncniIII,f'Hj nsyinincl ric sliMchni'50;)1 (in) 5051 (0) {)' fnmhiiiu'nlill5047 (jn) 5050 (sli) m' rniulmncnt idH055 (in) 5055 (2) p a' fiiriflmncntal:)082 (m) n/ rnmlnnK'iilnl5152 {w ) 1557 1 I5!)7' 515 ! ( \^)5581 (in) 2 1505 55!)2 (A )T^ rM'iistoiii 11)57) and iJ-, 15- and 4-acntylpyridijK' aro collncii d^ in lal)ln I Tlu^  lasor Kanian s]»oc‘iia and tlir portions ol’ th(‘ inriann) spr< tra ( ]^500-500 cm"^ ) in llio liipiid st-at,(‘ arc rcynodnond in Figuios 1(a). (li) and (c) and Kignros 2(a), (b) and ((*) r(\sp(H!t'ivoly.Ka(4\ (>r tli(' 1hrt*(' isoinorir ac‘(dylpyridin(  ^ inokaailt's is assunnal to hrivo tlu^  r.s-symimd ry, and tlin forty-t wo norma) rnodrs <d'vibrat ion are dislribnted amongst tlin sy»ninctry spncnos as follows ;28a' "f 14a"Ar<H>rding to tho solertion rulos all tlu^  vibrations air active both in the infrared and Raman spoc^ tra. Wiilo the sjjecies a/ shonld givt^  rise io  polarized Raman lint^ s, the species a/' will have depolarized Raman line's.TabJo 4- Fimdiunonlal vibrational 1‘requoncios of pyr'idinr. 2-, D- andl-aotdylpyridijio[TIu' iatomal vibrations oC tbf> aeotyl t r^oiip aic not iju-lndodlVihraUoifial spe c^tra o/ 2-, ^-and 4:-acetylpyridine 407Syniiiiol ry JMoflo No. (WilscmWavojinmbt'r (cm "i)(iaSni)oIIIISiillhi:i(ii> 71. SI. 11 •ISh U)l) :^ oi) 1 Oil 1 <»a I7n 4 T)I0f>nJObpyridine00 :ii;.s:i12JS 1030 (sor.4) lOliS 1482 3030 (1218) 052 (3030) 1572 1375 11 IS 1085 143!) 3083 SHO 371 981 749 942 ,880) 700 405-Acciyb)yi‘idinf'3-Ac(4 \ ]- p>'i idim'4-Ac(’t> 1 pyridine99.5 ] 035 9933002 3059 3000(.590) (591) (589)15S5 1580 159(i1150 1127 1214750 751 739lOSO 1093 10841041 1078 10041 105 I47S 1494(3002) (30.5<)) 30171282 1242 1 207022 024 001(3002) 3053 30311509 1574 1 5571290 1272 13241101 Ills 111530(> 308 3041421 1420 MJO(3002) 3089 3.82(409) (405) (417)954 958 903700 704 000903 928 875779 809 817482 472 405103 104 100( ) Frequency agsignod more than once.” Frequency not observed.IfOO HOC1(a)Fig. 1(h)Z900 litO MO , .,\ laooRaman SMirtCcM 'JI’lg. 1(0)Kg. 2(a)k :11 i III'//// V' - ■1000 BOORAMAN IJIJIFT CCM'';!'■«. (210'V4ooABoo 600 ‘itoo%. (^ (0VH ralim M  sfedra. of 2-, 3-„«J 4.«et„lpgri<H„ 411Species a'Of the nineteen a' modee oi' vibration thai. can bo derived from pyridine, iour mvolve esBeutially etretcUing of the C-H bondB. The polarized Raman line observed at 3062 cm-i with its infrared eounterpart ai, 3060 em-> in 2-aeetvl- pyndme and the Raman shift at 3059 em-^  and the infrared bands at !W53 and 3089 cm  ^ m 3-aoetylpyridine, and the Raman lines at 3031 and 3066 c m a n d  the infrarod frequcncioK at. U047 and 3082 cnr^ in 4-ac'.otiylpyridiiU3 ai’o apRiguod lo the C-H valence oscillations. I’kc pairs of wcdl-resolved bands at 1560 and 1585 cm 1587 and 1574 cni"~^ , and 1597 and 1557 ein  ^ in the case of the three luole- oules respectively are j'oadily identilied witli tli liighest, i*ing sl.retching fretpien- cios. The next highest C-C (C-N) slretehing modes belonging to the a' class arc expected in the 1400cm~  ^ region, and they may he repioscnted by tbc infiarc^ d frequencies at 1421 and 1465 cm“ ,^ 1420 and 1478 enr^, and 1410 and 1494 enr^  ^observed in the throe isomers of acetylj)yj‘idinc rcsjKictively. The Raman spectra of 2-, 3- and 4-acol.ylpyridine sliow^  very iiitonso and Jrighly polarized lim^ s at 995, 1036 and 993 cm^  ^ respoctiv'-ely and t.hcy arc nnambiguonsly assigned to the ring breatliiiig mode. The remaining modc^  being derived primarily from carhon stretching juay ht^  ati.rihiitcd tn the obser ved fi rapiencjes at 1296, 1272 and 1324 cin“  ^ in 2-, 3- and 4-acetylx>5o idinc resx)ccti\^ ely.In juoiiosubstitnted pyridines tlua'c ai'c four* jilaiiai' modes whieJi i\w< nnar^  substituent-sensitive. Tims i.he i>olarized Raman lines ai 360, 590. 750 and 108(» cm'^  ^ in 2-acetylpyridiue, 364, 589, 739 and 1084 cm"' in 4 aceiylx)yridine and 368, 591 and 751 ciir*^  and the infi’aic'd band ol' mediimi strength at 1093 ill 3-acotylx)3^ ridiii(^  may he assigned to thesii modes. Tlii' remaining liindamentals belonging to this class are idonl.iiied with the polarized Itamaii lines r)bservod at- 022, 1044, 1101, 1150 aud 1282 eiir^ in 2-ae(5t3d[na idine, 624 and 1078 em~^  and the infrared hands at 1118, 1127 and 1242 em ' in 3-acet3dpyridine, and ilie polarized Raman lines at 1064, 1214 and 1267 em-^  and the infi ared bauds at 601 and 1115 cii“  ^ in 4-aeol;ylx>yridine.kSpecias a" ^ In th(^  ft" class thon^  would ()c (dght pjnirliiu’.-like modes. The Raman lines at 163, 164 and 100 eiiri in the case of 2-, 3 -  and 4-acetylj>3rridine respect ively are observed to be depolar ized. The corresjKmding iuliared absorption Iroqneneies ocoui* at 160, 162 and 158 cm-^ They may be associated with the lowest non- planuar ring angle deformation mode which is sensitive t.o the substituent.. Tin* remaining ft" fundamentals are assigned to the obsoriaMl frequencies at 409, 482, 700, 779,903 and 954 cm”  ^in 2-acetylpyridine, 406, 472, 704, 809, 928 and 968 in 3-aotyli)yridiue, and 417, 465, 664, 817, 875 and 963 cm“  ^ in 4-acotylpyridine, Those assignments are in close agreement with those made in the case of other monosubstituted pyridines (Green et al 1963). One fundamental belonging t<^6412 K. C- Medhithis class being either very weak or coincident with some other fundamental is left unassignod.The. internal vihraiionn o f the acetyl groupBesides these twenty-seven pyridyl frequencies, there would be fifteen other /nodes arising from the internal motions of the acetyl group. They may bo classified as follows ;(i) One C 0 stretch (a') and t-wo C ^  0 deformations—one in-plane (a') and one out-of-plane (a").(ii) One CHj symmetric {a') and two OHg asymmetric (a', a"') stretches, one CHg symmetric (o') and two CH, asymmetric (o', o") deformations, two CHg rocking modes—one in-plane (o') and one out-of-plane (o"), and one torsional mode (o") of the CHg group.(iii) One C-CHg stretch (o'), one C-CHg in-plano deformation (o') and one C-CHg out-of-plane deformation (o").The C = O stretching frequencies are readily identified. The intense infrared band at 590 cm~^  observed in the case of the three molecules is assigned to the C = O in-plano bonding mode, whilst the C —- 0  out-c)f-plano deformation may bo responsible for the infiareci fi'(iquoncios at 409, 405 and 417 which arc already assigned to another fundamenta], in the case of 2-, il- and 4-acetylpyridinc respectively. These assignments are made in comparison with those proposed# for acetone (Harris & Levin 1972, Allkins Lippincott 1969, Cossee & Schacht- schueidor 1906). While the CHg stretching and deformation frequencies arc easily assigned, there remains some uncertainty in the assignment of the rocking modes of the OHg group. The observed infrared bands at 1018, 1023 and 1021 cm“  ^ in 2-, 3- and 4-acotylpyridiuo respectively are assigned to the out-of-plane rocking mode of the methyl group, and the in-plan© rocking mode may he re­presented by the Raman shifts at 953, 957 and 962 om"^ . Th torsional mode of the OHg group is, however, left unidentified. The C-CHg stretching and in-plane and out-of-plane bending modes are assigned respectively to the frequencies at 1238 395 and 215 cm*^  in 2-acetylpyridino and 1196 383 and 221 om"^  in 3-aoetyl- Xiyridino. In the case of the 4-isomer while the C-CHg stretching and out-of-plane bonding modes arc identified with the observed infrared bands at 1263 and 219 cni“  ^respootively, the in-plane deformation frequency is oithei- very weak or coincident with the fundamental at 365 cm~^ .Overtones and c o m b im tio n  bandsIn addition to the above fundamental frequencies, other weak bands are observed both in the infrared and Raman spectra. They may be assigned as overtones or combination bands of the fundamental frequencies.Vibrational spectra of 2-, Z-and i-acetylpyridine 413B17BBEN 0S6Alikins J, B. & Lippincott E. R. 1969. Spectrochim. Acta 2hAt 701.Berezin V. I. & Elkin M. B. 1973. Optica and Spectroscopy 84, 395.Ooflsee P. & Sohftchtflchneider J. H. I960. J. Chem, Phya. 44, 97.areen J. H. 8., Kyiiastou W. & Paisloy H. M. 1963. Spectrochim. Ada 19. 549.Harris W. C. & Levin I. W. 1972. J. Mol. Spectroaco. 48, 117.Hideyo Shindo 1957. Phatm. Bull. [Tokyo) 5, 472.Katritzky A. R. & Gardner .1, K, 1958. J. Chem. Son. 2198.Katritzky A. R. & Hands A. R. 1968. J. Chem. Soc, 2202.Katritzky A. R., Hands A. R. A Jones K. A, 1958. J. Ghm. Soe. 3165.Long B. A. & George W. 0. 1963. Spectrochim. Acta 19, 1777.Medhi K. 0. A Mukherjoe B. K. 1965. Spectrochim. Acta 21, 895.Medhi K. C. 1905. OpHka i Spektronhopiya 19, 49.Medhi K. C. 1972. Ind. J. Phya. 46, 300.Mrosfl W. D. Sc Zuridol G. 1970. Spectrochim. Ada 26.4, 1097.Spinner E. 1903. J. Chem. Soc. 3860.Wilmshui'st J. K. & Bernstein H. J. 1957. Can. J. (Jhem. 85. 118.1,Wilson E. B. 1934. Phya. Pcv. 45, 706.

The Vibrational Spectra of 2-, 3-and 4-Acetylpyridine

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The Vibrational Spectra of 2-, 3-and 4-Acetylpyridine

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