DAr HQC GrA Harr0r Qudc VIETNAL NATI0NAIttt'ttVERSITy, HAXOT t55N 6.6g 6t z ffiffiffi JE URNAL KH0A H0GTUN NMURAL SCIE TAP CHI KHOAHgC DHQGHN,KHTN & CN, T.XXil],S6 1,2007 NGHIENctltr tdxc Hdp vA rrTA NANCUCCHfr alv tvroNKrMLoAr ctia uOr sd nnNzoyLHIDRAZoNoHit*o"taoroPHENoN Nguy6n Minh Thio, Ph4m Vin Nhi6u, Nguydn Thi Thu Hrtong, Hd Thi Vdn, Vfr Phuong Li€n Khoa H6a hgc,TnrirngDqi hpel{hoa hqc TVNhidn, DHQGHN Trong thdi gian gdn d6y c6c nhi H6a hgc Nam Hin c6 mQt th6ng b6o [1]vd khA nlng rlc chd in mdn kim logi cira mQt sd hidrazon di tr] o- hidroxiaxetophenon v]r hidrazit ctra c6c axit benzoic thd Chfng t6i da m6 rQng vi ph6t tridn phrrong htr6ng nghiOn crlu niry vi dd c6 mQt sd c6ng bd 12,3, 41 Trong bdi b6o niry chfng t6i tidp t+c th6ng b6o sqr dng hgp c6c hidrazon hldng tg, di tr} cdc metyl o-hidroxiaxetophenon v6i hidrazit cria c6c axit benzoic thd: +H2N-Mr-""€" s -q;*_*_TOl *q; (I 1,2) (II1-5) 0II1-8) d d6y: I: 1) 4-CHg;2) 3-CH3 II: R: H, m-CH3,o-NO2,m-NO2vh p-NO2 C6c hgp chdt Ir, , dugc di6li chd trl m-crezolvi o-crezol th6ng qua phAn rlng este h6a rdi chuydn vi Fries nhiQt dQcao (160-1800C)v6i nh6mclorua khan lim xric t6c [5] Hgp phdn hidrazit (II1j nh{n dugc tfi c6c axit benzoicthd qua phin rlng este h6a th6ng thrrdng rdi tidp theo ld phin rlng gifla estevdi hidrazin hidrat 86% I2l TrI hai hgp phdn tr6n v6i ti lQ mol 1:1 dun s6i hdi lttu tt - gid etandl tuy6t d6i s€ nh{n drrgc sin phdm cu6i cring (IIIr J, md chring d6-utAch drr6i d4ng tinh thd dun s6i h6n hgp phin rlng Kdt qui ttugc gi6i thiQu bing Bing C6c benzoylhidrazon o- hidroxiaxetophenon (lll r.!) :;.-*."* 68 69 Nghi€ncriutdnghgpvd ntng rlc chdtn mbnkim loqi STT Vitrf CHt Vitri R 3_CH3 H 3_CH3 3_CH3 3_CH3 3_CH3 Higu sudt, ton", oc Phdhdngngoqi,cm'l To Vox Vrn Vc=H vco 168-169 85 3243 3028 1602 1643 m_CH 148-149 85 3228 3070 1602 1644 o_NO, 120-12',1 70 3213 3086 1604 1651 m_NO2 196-197 75 3213 3122 1606 1646 't91-192 82 3262 3108 1602 1650 P-Noz 4_CH3 o_NO, 123-124 70 3298 3213 1614 1659 4_CH3 m_NO2 269-270 75 3202 3029 1609 1643 220-221 82 3209 3009 1599 1647 4_CH3 P-Noz Vruoz 1528 1349 1526 1346 1518 1345 1564 1348 1529 1348 1519 1354 Tr0n phd h6ng ngo4i cria cdc hidrazon nhfln drrgcd6:uthdy xudt hign cdc v4ch d{c trdng cho dao dQngh6a tri cira nh6m OH phenol E 3202"8298cm'l, cfra nh6m NH amit 3009.-3213 cm'r, cria C=N L599-1614cm-r,cria nh6m CO amit f0+g-f059 cm'l, vA crianh6m nitro 1518-1564cm'r vA 1345-1354 cm'l TrOn phd IH-NMR th{y xudt hiQn cic tfn hiQu irng v6i chuydn dich h6a hgc cira c6c proton phAn t&: 6*1: 13,15- 13,67ppm; 6es: IL,23 - 11,60ppm; 6gH3:2,2! 3,30 pfm; cdn c6c proton thom c6 chuydndlch h6a hgc 6,80 - 8,?4ppm.Birig'3 ehi lai c6c drl kiQn vd ptrd rH-MvIR cria mQt sdhidrazontdnghgp drrgc Blng Phd TH.NMR cia mQtsdhidrazon ?:N-*H-co cHr Tqtpchi Khoa lwc DHQGI I N, RHTN & CN, T.nil il, Sd I, 2N7 70 ill Nguy€n Minh Thio, Phlm Vln Nhi0u Vitrf CH3 R Phd rH-NMR (6 pp,) 2,48(3H,C-CH.);3,30(3H,CH.);6,81(1H,Cu_H); 7,2O(1H, 3-CH3 H Ca_H);7,48(1H,C-H); 7,55(2H,C-H vA Crt_H);7,63(1H, OH);13,67(1H,_NH) C,o_H);7,94(2H, C-H vi C,-H); 11,28(1H, 2,41(3H,C-GH.); 2,48(3H,CHr);6,81(1H, 2,21(3H,Ce_GH3); 3-CH3 m-CH 7,49(1H,' Cu_H); 7,20(1H,C-H);7,44(2H,Cn_HvA C,o_H); C,,_H);7,75 (2H,C-H vi C,-H); 11,23(1H,OH);13,67(1H,_NH) 2,22(3H,G-CH.); 2,52(3H,CH.);6,82(1H,CrH); 7,22(1H, 3-CH3 m-NO, (1H,Co_H);8,38(1H,C,n_H);8,47 C-H);7,50 (1H,C.'.,_H);7,86 (1H,C-H); 11,60(1H,OH);13,56(1H,_NH) 2,22(3H,C-CHJ;2,51(3H,CH.);6,82(1H,Cu_H);7,22(1H, 3-CH3 P-Noz C.-H);7,52('lH,C-H);8,19 (2H,C-H vi C,'z_H);8,37(2H,CLH vAC',_H);11,61(1H,OH);13,55(1H,_NH) 2,29(3H,C-CH); 2,50(3H,CH.);6,85(2H,CLH vd C-H); 7,55 4-CH3 m-NO, (1H,Cu_H);7,83(1H,C'_H); 8,40(2H,C*H vA Cto_H);8,74(1H, C,-H); 11,58(1H,OH);13,20(1H,-NH) 2,29(3H,C-CHr); 2,50(3H,CH.);6,75(2H,Ca-Hvit C-H); 7,54 4-CH3 P-Noz (1H,Co_H);8,17(2H,C-H vi C.,z_H);8,38(2H,C-H vAC,,_H); 11,57(1H,OH);13,18(1H,_NH) TrOn phd khdi luOng cria mQt sd hidrazon thdy xudt hiQn pic ion phAn trl c6 sd khdi phrl hgp v6i phdn trl khdi vi c6c pic kh6c c6 sd khdi phi hgp vdi cic ion minh so dd phAn minh: + Hgp chdt III2 (mlz\:282 (M), 267,163,148,133, 720 (100%),119, 105,91,77, 65, 51 + Hgp chdt IIIa (mlz):313(M), 298,296,165,163,150 (100%), 148,134,133,1.19, 105,104,76,50 + Hqp chdt 1116 (mlz):313(M*), 298,296,179,163,150,148, 134,120 (100%),105, 104,92,69,55, 50 Tr) cic sdliQu tr6n, c6 thd d6n so dd phAn minh chfnh cria c6c hidrazon nhu sau: Tqpchi KhoahocDHNH N, KI{TN & CN, Tffi II, SdI, 2007 Nghi0ncfu t6nghqp vl nangrlc chdin mbnkim loqi 7l d\(o' "'t\l\f :N-M "-[fuil+ cHr \/ M* (\("" u^ H'c-\l\;-,.- ,/" v 't:v-*"-.-@*-h" ILco ., k*, ",.\l\ ; 'f:n-i'" I""'- | oH N t-un * r 1"","" -A(* "'\l\ r{r l * , ft1* ,S-r- '_.o.- \ | + _O -z , \ -@' ,^","{'lL -N-l+ tr-! -q \:zNl* * v H "g l "o l'* 'fr' -,-*fil ",.fi rl Nhu vfy, c6c dfl kiQn v6'pfrd da x6c nhsn cdu t4o c&a c6c hidrazon tdng hqp drrQc ld dring vA hoin toirn pht hgp v6i c6c kdt quA nghiQncrlu dd dtrqccdng bd t2l Od ntao s6t ning itc chd trn mdn kim logi cria c6c hidrazon tdng hgp dtrgc, theo phrtong ph6p kh6i lrrgng, ddi vdi th6p CT-3, nghia lh cho ' chfng t6i de thrl nghiQm th6p CT-3 vio dung dich axit HCI 2M kh6ng c6 (m5u so s6nh) vA co chdt rlc chd ctng mQt thbi gian, rdi x6c dinh mrlc eiim khdi lrrgng cira c6c tdm th6p, til d6 rrit drrgckdt lu{n v6'khi n[ng r1cchd 6n mdn kim lo4i ctra c6c ch{t nghidn cilu, d{a tren str tfnh to6n theo cic c0ng th0c sau d6y: +TdcdQinmdn: y =(m,-m) - L^ s.r s.t Trong d6: me,m: khd lrrqng t{m th6p CT-3 tuu6cvi sau thf nghiem [g] S: tdng diQntfch c6c b6'm{t t{m th6p CT-3 [cm2] t: thdi gian thi nghiQmbhftl Tsp chi KhoahpcDHQGHN,KHTN & CN, nffill, SdI, 2Un Nguy6nMinh Thio, PhamVen Nhi€u 72 + HO sdin mdn: = Y * tooyo ' y o " Trong d6: V6, V : tdc d0 dn mdn trddng hgp kh6ng c6 vi c6 (tuong fing) ch{t tlc chd + HiGusudt bio vQ:F/o =Vo-]-V *I00o/o= (l0o - y)% vo Kdt qui thrl nghiQm drrgcddn & bing sau diy: chdngln mdnth6pCT-3trongm6itrudngHCI2Mc0acic hidrazon Blng Kdtqul thfi nghiQm \a, DeiluglSV "t Po/o 29,40 5,76 4,26 9,00 8,28 7,80 6,70 3,86 5,52 100 19,59 14,19 30,60 , 26,53 23,08 13,28 17,02 80,41 85,51 69,40 73,47 76,92 86,72 82,98 71,84 I Nhrr v{y, t{t cA c6c hidrazon tdng hgp drrgcd6luc6 ning itc chd dn mdn kim Io4i v6i mrlc dQkh6c (hiQusudt b6o vQtt 69,4- 86,7%) Th{c nghiQm * Tdng hqp S-vi 4- metyl - 2- hidroxi axetophenon( ILz )[5] Di til o-cresolvi m-cresol qua phin rlng este h6a bing anhidrit axetic rdi chuydn vi Fries tidp theo [5] v6i Alcls khan lhm x6c tdc HiQusudt: gO-g4% t!:2l|oC o-cresylaxetat m-cresylaxetat HiQusudt: 9Q- 94o/o t! :2l0oC 3-metyl-2-hidroxiaxetophenon HiQu sudt:75% t! :1750C 4-metyl-2-hidroxiaxetophenon HiQusudt: 71% r! :1600C * Tdng hep c6c hidrazit cia c6c axit benzoic thd ( IIr E) [2] C6c hidrazit drrgc tdng hqp tr] axit benzoic thd qua hai brr6c: este h6a th6ng thudng (t6c dgng v6i aniol c6 xric t6c axit) rdi tidp theo cho este phin itng v6i hidrazin hidrat 85% dun s6i etanol Nh4n dugc: 1) Etylbenzoat HiQusudt:82% t!:212-2140C Tsp chiKhoa hpcDHQGHN, KIIT N & CN, T.)Wil, SdI, 2007 fc chd nn mbnkim 2) Metyl m-toluat , HiQusudt: 65% t!:2l5oC 3) Etyl o-nitrobenzoat HiQusudt: 72% t!:2L5oC 4) Metyl m,nitrobenzoat HiQusudt:65% t!:78-790C 5) Metyl p-nitrobenzoat Hi6u sudt: 65% to,296-97oC 1) Hidrazit ctra axit benzoic HiQu sudt: 80% -l { : 109 lOoC 2) Hidrazit cria axit m-toluic HiQu su{t: 93% t! :90-910C 3) Hidrazit cira axit o-nitrobenzoic Hi0u su{t: 80% t! :120 -l2lo C 4) Hidrazit cfra axit m-nitrobenzoic Hii.,.rrft, OOX tl :165-16dC 5) Hidrazit cria axit p-nitrobenzoic HiQu sudt: 82% t!:215-2l6oc CAcHidrazit: * Tdng hQp c6c hidrazon di tfi 3-(hoic 4.) metyl-2-hidroxiaxetophenon c6c hidrazit cta c6c axit benzoic thd (IIIr,8) vdi Dun s6i hdi luu hdn hqp cria 0,025 mol 3- (ho{c -) metyl-2-hidroxi axetophenon v6i 0,025 mol cria hidrazit axit benzoic thd etanol tuyQt d6i Ldc ddu h6n hgp phin rlng tan hdt Sau d6 sAn phdm phin rlng hinh thAnh vi t6ch dqng chdt rdn tinh thd dun n6ng Lgc n6ng, rrla bing mQt it etanol n6ng Dd kh6 ngoli khdng khf, cAn vi tinh hiQu su{t Kdt qui dugc trinh bny bAng Kdt luQn Dd tdng hqp duo.cmQt ddy hidrazon di tt c6c metyl o-hidroxiaxetophenon v(n che hidrazit cria e6c axit benzoic thd Cdu t4o cria cdc sin phdm di du-o.cx6c clinh nhi phd hdng ngoqi, cQnghtr8ng tt pr6ton vi phdkhd lugng T{t ci c6c hidrazon nhgn dugc ttdu c6 khA ning rlc chdin m6n th6p CT-3 mOitrudng HCI 2M u TAr LrSU THAL KHAO A S Fouda, M M Gauda, S I Abd El-Ratimarr, Bull Korean Chem, Soc., Vol.21, 1f11, (2000), 1085 Nguy6n Minh Th6o, Vfr Minh TAn, Phqm Vdn Nhitu, Tgp chi H6a hgc,T.42, If3(2004), tr 11 Ph4m VIn Nhi6u, Vfr Minh Tdn, Nguy6n Minh Thho, Tg.p chi Ph6n tich H6a, L! vd Sinh hgc, T 9, lf2(2004), tr 42 Tqpchi Khoaho.c DHQGHN, KHTN & CN, T)N II, SdI, 2M7 Nguy€nMinhThio,PhemVnnNhiOu 74 NguySn Minh Th6o, Phgm Vin Nhi€u, Nguy6n Mgnh Cuing, Tqp chi H6a hgc vd tng dVng, T{7 (2005), tr 35 Nguy6n Minh Thio, Ng.,y6tr Dinh Thinh, Dlng Nhrr Tgi, D[ng Quttc Thanh, Nguy6n ViQt Ttr{ng, Hoing Kim Vdn, Nguy6n Thu Lan, Phan Vin Cu,Ta.pchi H6a hQc,T.}l, No8(1997), tr.17 VNU JOURNALOF SCIENCE,Nai.,Sci., & Tech.,TJqlll, Nol, 2007 STUDYON SYNTHESTSAI{D METALLIC CORROSIONINHIBITION OF SOIUEBENZOYLHYDRAZONESO TIYDRO)ffACETOPHBNONES Nguyen Minh Thao, Ph4m Van Nhieu, Nguyen Thi Thu Huong, Ho Thi Van, Vu Phuong Lien Department of Chemistry, Collcge of Sci,ence,VNU Some hydrazones from hydrazides of substituted benzoic acids with ohidroxyacetophenones have been prepared by the condensation of hydrazides of substituted benzoic acids vrith o - hidroxyacetophenones IH-NMR and MS The structure of these products have been determined by IR, spectroscopies Tqpchi KhoahqcDHQGHN, KI{TN & CN, T)Oilil, Si I, 2N7 VIETNAM NATIONAL UNIVERSITY, HANOI JOURNAL OF SCIENCE NATUMLSCIENCES & TECHNOLOGY T XXIII, No1- 2OO7 CONTENTS l Vu Duc Minh Some new experiment results applying combination of the electrical souriding methods in order to discover old vestiges 2, Le Duc Manh, Nguyen Thi Huong Giang Appiication of PCR techniquefor detectionof Salrnonellain polluted surfacewater Lz Pham Ngoc Lan, Luu Van Boi Amphiphilic polyurethanes with a novel peg-containing chain extender part I: Synthesis and characterization) Hoang Thu Ha, Pham Thi Tran Chau Study on trypsin inhibitor (tI) and chymotrypsin inhibitor (KI) from seeds of blue dragon (Hylocereus undatus (Haw.)Britton & Rose) D Mai Trong Nhuanr, Tran Dang Quy, Nguyen Tai Tue, Dao Manh Tien, Nguyen Thi Hong Hue, Nguyen Thi Hoang Ha Study characteristics of sediment environmental geochemistry of Phan Thiet - Ho Tram near-shoreZonef.orsustainableuse of natural resources 19 Q A da Nguyen Kien Cuong Plasma-InducedGraft Polymerization of Acrylic Acid onto Poiy(ethylene terephthalate) Films: Hydrophilic Modification 47 Tran Minh Hanh, Nguyen Quoc Tuan, Luu Cam Loc Photooxidationof p-xyieneon TiO2and modified-TiO, catalysts ,, ,, o t Nguyen Minh Thao, Pham Van Nhieu, Nguyen Thi Thu Huong, Ho Thi Van, Vu Phuong Lien, Study on synthesisand metallic corrosion inhibition of some benzoyl hydrazonesohydroxyacetophenones, , , ... v6i hidrazin hidrat 85% dun s6i etanol Nh4n dugc: 1) Etylbenzoat HiQusudt:82% t!:212-2140C Tsp chiKhoa hpcDHQGHN, KIIT N & CN, T.)Wil, SdI, 2007 fc chd nn mbnkim 2) Metyl m-toluat , HiQusudt: 65%... near-shoreZonef.orsustainableuse of natural resources 19 Q A da Nguyen Kien Cuong Plasma-InducedGraft Polymerization of Acrylic Acid onto Poiy(ethylene terephthalate) Films: Hydrophilic Modification 47 Tran Minh... I, 2N7 VIETNAM NATIONAL UNIVERSITY, HANOI JOURNAL OF SCIENCE NATUMLSCIENCES & TECHNOLOGY T XXIII, No1- 2OO7 CONTENTS l Vu Duc Minh Some new experiment results applying combination of the electrical