TAI' CHI HOA HOC " T.50(2)133-139 THANG 4 NAM 2012
T6NG HOP VA TINH CHAT QUANG
CUA MOT S6 DA'N X U A T 2 - P I R A Z O L I N TU" AXETONPham Van Hoan', Vii Quoc Trung', Luong Lieu Thuy^
'Khoa Hod hoc - Dgi hgc Sir phgm Hd Ngi 'Sd Gido due vd Ddo tgo Lgng San
Den Toa soan 26-01-2011 Abstract
Ten compounds containing 2-pyrazoline liclerocycle were synthesized by reaction of a,p-unsateraded ketones with hydrazine or its derivatives. Structures of the synthesized compounds were comnrmed by IR. NMR and MS spectra These compounds showed the interesting fluorescence properties in the region of visible light.
Keywords: Pyrazoline, heterocycle, a,p-unsaleraded ketone, fluorescence, acetone.
1. DAT VAN DE
Hda hpc cac hgp chat dj vdng la mpt trong nhirng nganh khoa hpc phat trien manh ciia Hda hpc Hiru ca, chiing khdng chi phong phu ve so lugng, da dgng ve chiing logi ma ngay cang co nhieu hgp chat dugc ung dung vao cuoc sdng. Nhieu hgp chat loai nay (pirazolin, flavonoit, pirimidin,...) cd nhifng dgc tinh sinh hpc da dgng nhu khang khuan, chdng nam, chdng lao, chong ung thu, chong HIV cung nhu linh chat quang hgc thii vi... Cac nghien ciru da cong bo cho thay, cac hgp chat chua di vdng pirazolin cd nhieu ung dung quan trpng nhu dieu che thudc gay me, chong suy nhuge, trj benh ve than kinh...[1-3] va kha nang uc che nhieu logi vi khuan khac nhau: khang nam, khang kliuan va chdng cac qua trinh oxi hoa.
Trong cac dan xuat ciia pirazolin, 2-pirazolin dugc nghien curu nhieu hon ca. Di vdng 2-pirazoIin la mdt vdng khdng phang 5 cgnh, gdm 2 nguyen tu nita, trong do cd mpt nguyen tCr nita lien ket ddi vdi nguyen tii"
cacbon. Day chinh la nguyen nhan lam cho cac hgp chat chua dj vdng 2-pirazolin cd kha nang phat quang
[4, 5]. Vi vgy cac hgp chat kieu l,3,5-^triaryl-2- pirazolin cdn cd the dimg lam diot phat quang va la chat van chuyen cac Id trdng trong vat lieu ban dan img dung cho pin mat trdi [6, 7]. Nghien ciru va ting dung cac vat lieu phat quang la mpt trong nhifng xu the phat trien cua khoa hpc ngay nay. Diot phat sang hifu Cff da tao nhieu san pham irng dung cho nganh cdng nghiep dien tir va dang dan thay the tinh the ldng trong cdng nghe hien thi (man hinh, panel quang cao, poster,...).
Vdi nhieu cdng nang nhu tren cac hgp chat chira dj vdng 2-pirazolin da va dang thu hiit dugc sir chu y ciia cac nha khoa hpc trong va ngoai ntrdc. Tuy nhien, nhieu tinh chat - dgc biet la tinh chat quang ciia chiing cdn it dupe nghien ciru.
2. THUC NGHIEM 2.1. Tong ho'p
Cac chat dugc tong hgp theo sa dd dugc mo ta tuang tu nhu trong tai li?u [8]:
CHaCOCHj HjNNHAr ArCH=0 1 1 ArCH=CHCOCH=CHAr -J. _ > . ^^._N
Ar: CfiHs-, 4-(CH3)3N-C6H4, 4-CI-C6H4-, CsHsCH-CH-; Ar': H, CsHj-, 4-02NC6H4- Phan irng tdng hgp cac xeton a,p-khdng no dupe
thuc hien nhu sau: }lda tan 0,002 moi andehit tham trong coc 100 ml bang 20 ml ancol etylic, them tilp
2 ml dung djch natri hidroxit 20% lam xiic tac, khuay tir khoang 5 phiit de chat ran tan het. Sau do them 0,001 moi axeton va tiep tue khuay trong 50
TCHH,T, 50(2), 2012
phiit. Chat ran tach ra trong khi khuay, Ipc rira ket tiia bang nudc, lam khd d nhigt dp phdng \k cac xeton a,^khdng no, Sau khi ket tinh Igi, san pham dugc do nhi?t dp ndng chay, kicm tra dg tinh khict bang sac ki ban mdng silica gel trong h? dung mdi la H-hexan va etyl axetat theo li Iv the lich thich hgp va do cac logi phd de xac djnh cau tnic.
Phan img tdng hgp cac hgp chfii chira vdng 2-pirazolin dupe lh\rc hi?n nhu sau: I Ida lan hon hgp gdm 0,001 moi va 0,00015 moi natri axctai trong binh cau 50 ml bing 20 ml axil axclic bang, them 0,003 moi phenylhidrazin, kluii'iy k? dc hdn hgp tan het. LSp sinh ban nudc. dun hdi luu trong 4 gid. De ngupi. sau 48 gid cd chat lan tach ra, Lpc. rira ket tua bang nudc, lam khd d nhi^t dp phimg va ket linh lai san pham b3ng dung djch clanohctyl axetat vdi
va Qudc Trung vd cgng su ti lp the lich ):!,
2.2. Ngliien ciru cau true va tinh chat Pho hong ngogi do dudi dgng vien nen vdi KBr iicn mky FTS-6000; Pho cgng hirdng tir hgt nhan ('ll-NMK) dugc do tren may BRUKER XL-500 trong dung mdi DMSO-d,, ho^lc CDCI3; Pho khoi lirgng ctia cac chat dugc do Ircn may Agilent 6310 Ion Trap tgi phdng Cau Irtic, Vi^n Hda hpc - Vien Khoa hgc va Cdng ngh? Vict Nam, Phd huynh quang phan tir tren may HP 340-LP 370 (Nhat Ban) dugc lai Trudng Dai hpc Khoa hgc Tir nhien - DIIQG Ha Npi. Budc sdng kich thich Irong qua trinh do la 325 nm 6 nhipt dp 300 K. Cac mau dupe do (V Irang thai ran.
Bang I: Mpi sd d?ic trung vat li ciia cAc xeton a,p-khdng no
Andcliit
Cl-4^^CHO
ch§I ran, Cc - 121,7°C
Q - C H O
chat long
N - Q - C H O
chat ran, 1 ^ = 75°C
chat Idng
Xeton a.[l-khdng no
ci-Q^^^Y^^-Q-ci
*-* ; linh the hinh k i m , mau vang nhat, t V - 196-196,5T, l l i v u s u a t 7 0 % .
I R ( c m " ' ) ; v'c.ii (benzen, anken) 3012,5; Vc-o. 1626,8; vc c{t>cnzen, anken) 1586,3; v,„„i_„.., 982,3; vc-ci 831
^ ; tinh the dang vay, mau vang t u a i , t ° „ = l l l - l l 2 ° C . Hieu suit 73%.
IR (cm"'): Vc.n (benzen, anken) 3055,5; \'c-o, 1651,8; Vc^c (benzen, anken) 1589,8; v „ „ , M „ „ , 981,8
'-' ; tinh the hinh k i m , may do sam, t V = 193-I93,5°C. K i hieu C. Hivu suat 65%.
IR ( c m ' ' ) : Vc.M (benzen, anken) 3025,5; Vc.n (no) 2896,3; Vc o, 1636,7; vc-c (benzen, anken) 1518,2 va 1596,3; v„,„i_,„,„ 986,4
0
^ ^ ; tinh the hinh k i m , mau vang d^m, ' ° „ = 148-I48,5°C. Hieu s u i t 72%.
IR ( c m ' ' ) : Vc.H (benzen, anken) 3036,4; vc-o, 1639,9; Vc.c (benzen, anken) I 5 7 2 , 7 v a 1591,4; v „ „ , i . „ „ , 998,2
K i hieu
A
B
C
D
1,2012 Tdng hgp vd llnh chdt quang...
Bdng 2- Mpt so dac trung vat li ciia cac chat chira dj vdng 2-pirazolin
Dan xuat 2-pirazolin Daii xuat 2-pirazolin
\J
Chat bpt mau vang tiroi, f.^ = 217- 217,5°C. Hieu suit 70%.
IR (cm"'): vc-ii (benzen, anken) 3045,9;
Vc-H no 2924,8; VC-CC-N 1491 va 1597;
v„.,i-,„,„1091;vc.a824
'HNMR(5, ppm):3,74(lH,dd,./= 17 Hz,J= 12,5Hz);2,96(lH,dd.J= 17,J
= 5,5); 5,51 ( l H , d d . J = 10,5,J=5,5);
6 , 7 5 ( l H , d , J = 16.5);7,40(lH,d,J=
12,2); 7,26 (2H, d, J = 4,5); 7,40 (2H, d, y = 2); 7,59 (2H, i,J= 8.5); 7,40 (2H, d, y = 8,25); 6,39 (2H, d, J = 8); 7,15 (2H, t, J = 8 , 5 ) ; 6 . 7 2 ( l H , l , y = 7 . 5 )
Tinli th^ mau trang, hinh kim, t V = 194- 195°C.Hi?usuat65%.
IR (cm"'): Vc-[i (benzen, anken) 3057,7; Vc.n no 2830,1; Vc,o 1649; Vc-c.C.N 1559 va 1593; v.,„,i _ „ 1085; vc-ci 823
'H NMR (.5, ppm): 3,67 (IH, dd,y= 17,7, J=
12);2,98(IH, d d , J = 17,7,7= 4,5); 5,49 (IH, d d , / = 1 2 , . / = 4 , 5 ) ; 7 , 0 0 ( l H , d , J = 16,5);
7,21 ( I H . d , , / = 18);7,18(2H,d,y=8,5);7,38 (2H, i,J= 8,5); 7,64 (2H, d, 7 = 8,5); 7,43 (2H,d,y=8,5);2,2(3H,s)
Tinh the dang hat, mau do gach. t „^ - 209,5-210°C. Hieu suat 60%.
[R(cm"'): vc-H (benzen, anken) 3055,5;
Vc-„ no 2935.5; VC.C,C-N l't90 va 1589;
v„„,n„., 1102; vc^, 835; VC-NO! 1302 'H NMR (5, ppm): 3,85 (IH, dd, J=
17,7,./= 12); 3,05 (IH, 66, J= 17,5, J = 4 ) ; 5 , 7 2 ( l H . d d , y = 12,7= I 2 , J = 4 ) ; 6,93 (IH, d , J = 16); 7,29(11-1, d,./= 16);
7,26 (2H, d , 7 = 8); 7,41 (2H, d, J = 8,5);
7,41 (2H, d, J = 8,5); 7,61 (2H, d, J = 8,5); 7,41 (2H, d, J = 8,5); 7,0 (2H, d, y = 8,5);8,04(2H, d, J = 9 )
Chat bot mau vang tuoi, t°„ = 153-153,5°C.
Hi?u suit 70%.
IR (cm"'): Vc-H (benzen, anken) 3022; VC-H no 2908,6; VC-CC-N 1499 va 1593; v„„,|.,„„, 953;
Vc-ci 835;
'H NMR (<5, ppm): 6,76 (IH, dd, 7 = 17, J = l2);2,97(IH,dd,y= 17,7= 5,5); 5,46(IH, dd,7= 12,7=5,5); 6,75 ( l H , d , y = 16,5);
7,23 (IH, m); 7,26 (2H, m); 7,33 (2H, m); 7,60 (2H, d, y = 7,5); 7,36 (2H, m); 7,27 (1H, m);
6,95 (2H, d, J = 8,5); 7,13 (2H, t, 7 = 7,5)
H,N-C-^-N
6
Chat bgt mau trang, d?ng hat, t V = 227- 228°C. Hieu suit 64%.
IR (cm''): Vc-H (benzen, anken) 3038,7;
Vc-H no 2953,3; Vc=o I645;VC=C.C=N 1551; v„„,,_,„„ 1168; v^m 3473 va 3295;
^NH2l599
H NMR (<5, ppm): 3,65 (IH, d d , 7 = 17,5,7= 12); 2 , 9 2 ( i H , d d , y = 17,5,7=
5); 5,39 (IH, dd,7= 12,7= 5); 6,90 (IH, d , 7 = I 6 ) ; 7 , 0 I ( I H , d , 7 = 16,5); 7,16 (2H, d , 7 = 7,5); 7,34 (2H, m); 7,24 (IH, m, 7 = 7,5); 7,57 (2H, d, 7 = 7,5); 7,38 (2H, m);7,31 (IH, m); 6,36(s)
HjC-C
6
Tinh the mau vang, dang hat, t V = 126,3- I27°C. Hi?u suat 62%.
IR (cm"'): Vc.H (benzen, anken) 3031,6; VC.H no 2939,1; Vc.o I655;vc.c,c-N I49I va 1562;
V„n,l-(,.n. 952
'H NMR (S, ppm): 3,68 (IH, dd,7 = 17,5,7=
12); 2,98 (IH, dd, 7 = 17,7,7= 4,5); 5,49 (IH, d d , 7 = I I , 7 , 7 = 4 , 5 ) ; 7 , 0 0 ( I H , d , 7 = I 6 , 5 ) ; 7,19 (IH, d , 7 = 16,5); 7,16 (2H, m); 7,33 (2H, t, 7 = 7,7); 7,24 (IH, t , 7 = 7,5); 7,60 (IH, d, 7
= 7); 7,37 (2H, t , 7 = 7,5); 7,30 (IH, m); 2,24 (3H, s)
135
TCHH.T. 50(2), 2012 va Qu6c Trung vii cong .sir Dan xuat 2-pirazolin
Tinh the iiKui do sam. dflng hflt; 1",,^ = 208-209"C. Ili9usuat60%.
IR (cm"'): V(..ii (benzen. anken) .1026.9.
Vc.n no 2927.5; Vl c,CNl492v:i 1594;
.',i,„M,.,„957;vs„. 1300
H NMR (A ppm): 3.86 (111, dd. 7 = 17,7.
7 = 12);3.12(111.dd,7= 17.5.7=4); 5.71 (IH.dd.7= 12.7=4); 6,79(111.d.7 = 16.5); 7,26 (111, m); 7.03 (211, d, 7 = 7.5);
7.35 (211, m); 7.28 (111, m); 7.61 (211, d. 7
= 7.5); 7,38 (211, m); 7.31 (111, m); 7.03 (2H.d.J-8.5):8.0(2ll.d.7 = 9)
Dan xuat 2-pirazolin
Tinh the hinh que, mau ving Hic, t",,^ = 1 7 1 - 172"C. Ilitusu.lt65%.
IR(cm"'): vc.ii (benzen, anken) 3026,8; vc.ji no 2819va2898;v, ,, 1656;v, t c - N l 5 2 4 v a K'(M;v,„„i,„„„953.
'lI NMR (rf. ppm): 3,54 (III, d d , 7 = 17,2,7=
12.2): 2.89 (111, t, 7 = 4. 7 = 3); 5,33(IH, dd,7
= 11.2,7=4); 6,86(111. d . 7 ' 16.5); 6,91 (IH, d. 7 = 16,5); 6,96 (211, d, 7 = 8,5); 6,63 (2H, d, 7 = 9); 7,43 (211, d, 7 = 8,5); 6,69 (2H, d, 7 = 8,5); 2,93 (611, s). 2,84 (611, d); 2.20 (3H, s)
Ki hieu
Tinh the mau vang dam, dang hat, t"i,c = 112.5-113°C.Hi9U suat 70%.
IR (cm"'): Vc.n (benzen. anken) 3022,1 Vc.H no 2893.6; vc c C-N 1541 \a 1584;
v„n,i-,,d.,983;vNH3321,
'HNMR(5, ppm): 3,01 (IH. d d . 7 = 16, J = 10.5); 2,60 (111, dd. 7 = 15,7, 7 = 9.5); 4,36 (IH, dd, 7 = 18,5. 7 = 9,5);
6.62(1 H, d. J=16); 6.50 (IH. dd, 7 = 15,5, 7 = 10.5); 7,70 (111, dd. 7 = 15.5.7
= 10,5); 6.69 (IH. d, 7 = 16); 6.29(IH.
dd. 7 = 16, 7 = 8); 6.55 (HI. d, 7 = 16);
7,53 (2H, d. 7 = 7); 7,33 (211. m); 7.23 (IH, m); 7.48 (2H. d, 7 = 7,5); 7,33 (IH.
m); 7,33 (III, m)
9"
0,N
215,3- Tinh the hinh kim, mau vang dam, 1°^
215,7"C. Hi?usuat65%.
IR (cm"'): Vc-H (benzen. anken) 3038,8; VQ-W no 2911,6: vc c c N 1549 va 1582: v,„„,.,„^ 985 VNO.^1298.
3. KET QUA VA TI IAO LUAN 3.1. Tong ho'p va cau true
De tranh vice thu dtrgc san pham ngung ty mgt lan, hpp phan andehit dugc \ky hai du va keo dai thdi gian phan irng. Tuy nhien do li6n hanh trong mdi trtrdng kiem nen khi keo dai thdi gian phan irng cd the xay ra qua trinh ty oxi hoa khu ciia andehit theo phan ung Cannizaro se lain giam hieu suat phan ijng.
Thdng thudng, nhiet dp ndng chay ciia hgp chat chiia dj vdng 2-pira2olin cao han xeton a,p-khdng no tuang ung do phan lij khdi tang nhieu. nhung nhiet dp ndng chay cua A3, C3, D3 lai thSp han xeton a,|3-khdng no tuang ling; B3 cd nhiet do ndng chay cao hon B khdng dang ke. Trong nhu^ng trudng
hpp nay cd Ihe tinh cdng kenh ciia phan tiJr chi phoi:
phan lir cdng kenh nen nhi9l dp ndng chay thap. Khi cho xeton a.p-khdng no lac diing vdi hidrazin trong dung mdi la axit axetic b5ng/natri axetat se thu dugc san pham axelyl hoa tgi vi tri nguyen tii N ' [8], Khi sir d^ing dung nioi ancol etylic cd them may gipt axit 1ICI dgc d3 thu dugc san pham khdng bi axetyl hoa (tochat D3). Ket qua nay cho thay qua trinh cpng eleclrophin vao lien ket ddi C=C xay ra rat nhanh, xay ra ngay sau khi qua trinh ngung tu-tach nudc xay ra, vi da khdng thu dugc san pham kieu AriC-N-N=CAr2.
Vi^c tdng hgp B4 cd ddi chut khd khan so vol cac chat cdn lgi. Trong moi trudng ancol etylic/HCI khdng thu dugc 84 ma chi thu dugc san phSm ngung ty dang -CH=KNHAr' dijkeo dai thdi gian dun ndng; khi thay bang axit axetic/natri axetat thi
TCHH,T, 50(2), 2012
B4 dugc hinh thanh, dieu dd chiing td phan irng phu thupc vao nhi?t dg, hay ndi each khac, phan irng khep vdng bi khong che nhiet dpng. Dieu nay cting gop phan khang djnh qua trinh tao vdng di qua giai doan dau la phan ung ngung tu loai nudc giifa hidrazin/dan xuat hidrazin vdi xeton trudc khi xay ra
Tang hgp vd tinh chdt quang...
qua trinh cgng electrophin ciia nhdm NH vao lien ket doi C=C theo kieu cdng Mai-can [8]. Phd MS ciia chat A3 thay xual hien pic M+Na = 382 va pic M' ^ 359 vdi cudng dp ttrong ddi manh, chiing td ion phan tu nay tuang ddi ben va phii hgp vdi phan tir khoi dy kien.
9
1 3 X2 1 1 10
/^H/ii: Pho'H NMR ciia D4 Tren phd IR ciia cac chSt chua di vdng
2-pirazolin khdng cdn van dao ddng hoa trj ciia lien k^t C=0 trong phan tir xeton a,f3-khdng no tuong ling; Tren phd ' H NMR xuat hien 2 cum tin hieu rat ro rang khac so vdi xeton a,p-khdng no ban dau, Cac proton dgc trung cua vong 2-pira2olin cd tin hieu cpng hudng nhu sau: SH^^ = 3,01-3,86 ppm (dd); JH4b= 2,6-2,97 ppm (dd); 3^5 = 4,36-5,72 ppm (dd) phil hgp voi cac tai lieu tham khao [2, 8]. Ngoai ra, neu trong phan tii cd them cac proton khac nhu -NH, -CH3 hogc C=0 thi cung rat de dang nhgn thay. Phd ' H NMR cua chat D4 kha phtrc tgpnhung vSn thay cac tin hieu proton ciia vdng pirazolin cung nhu tin hieu ciia mdt sd proton dgc trung khac (hinh 1).
Nhu vay, k8t qua phan tich phd hdng ngogi, cpng hudng tir hat nhan cho thay cac chat thu dugc phil hgp vai du kien va khang djnh sir tao thanh cac chit chiia di vdng 2-pirazoIin.
3.2. Tinh chat quang cua cac chat chiia di vong 2-pirazoIin
Mgt s6 chdt chira dj vdng 2-pirazolin thu dugc the hien tfnh chSt phat quang ngay trong dung djch d dieu ki?n thudng. De danh gia khach quan, phd
huynh quang ciia cac chat dugc nghien eiru d trang thai ran. Ket qua dugc the hien tren bang 3.
Hinh 2-5 cho thay, cac chat chira di vdng 2 - pirazolin deu phat quang trong viing kha kien 425- 580 nm (vting anh sang xanh —* vang) khi dugc kich thich vdi budc sdng thich hgp. Nhung eye dgi huynh quang va cudng dp phat quang cua cac chat cd su khac nhau.
Tir so li?u d bang 3 cho thay cd nhieu yeu td chi phdi eye dai huynh quang va cudng dp phat quang cua di vdng 2-pirazolin. Nhu vay cd the thay rang:
dinh huynh quang ciia cac chat phu thupc vao mat dp dien tieh trong vdng 2-pirazolin va nguyen nhan chinh la sy cd mat ciia cac nhdm the khae nhau.
+ Khi X', X^, X^ day electron mgnh, eye dgi huynh quang chuyen djch ve phia sdng ngan hpn nhung cudng dp phat quang tang.
+ Khi X , X^ day electron mgnh, X^ hiit electron, eye dgi huynh quang chuyen dich ve phia sdng dai, cudng dp phat quang giam.
+ Khi X', X^ hilt electron. Nlu X^ day electron:
cue dai huynh quang chuyen djch ve phia sdng dai, cudng dg phat quang tang. N^u X^ hiit electron thi eye dai huynh quang ciing chuyen dich ve phia sdng dai va cudng dp phat quang giam.
TCIIH,T. 50(2), 2012 va Quoc Trung va c0ng str
" % TO m TO HB ( W —
T B I — g e o — H D — n o
Hinli 2. Pho huynh quang cua M , A3, A4 485
450 '^
A-'
Wnli 3: Pho huynh quang ciia BI, B2, 83, B4
525
I •
Hmh 4 Phd huynh quang ciia A3, B3, C3 Hmh 5: Phd huynh quang cua 0 3 Bdng 3: Bang quy ket phd huynh quang phan tir cua mpt so chat
X'- ' — ' ^ '
X'
4-ClC6H(-
CsH,-
4-(CH3)2NC6H,-
X-
4 - d C6H,CH=CH-
C6HiCH=CH-
4-(CHj)2NC6HjCH=CH- X' C.H,- CHjCO- 4-NO,C6H4-
CeHs- H2NCO- CHjCO- 4-NO;C6Hj-
CHjCO-
Ki hi?u Al A3 A4 BI B2 B3 34 C3
^iTux(nm) 470 430 580 480 425 450 575 485
Cuong do 16000
1300 800 12000 23000 5300 600 6250 Nhu vgy, sff bp nghien ciiu ve sy anh hudng ciia 4. KET LU/^N
cac nhom the den cue dai huynh quang va cudng dp phat quang ciia dj vong 2-pirazolin cho thSy: X', X^, X^ ciing day electron thi eye dgi huynh quang chuyen djch ve phia sdng ngSn, cudng dp phat quang tang (B2) hogc ciing hut electron thi cue dai huynh quang deu djch chuyen ve phia sdng dai, cudng dp phat quang giam (A4).
Bang cdc phuang phap truyen thong da tong hpp dugc 4 xeton a,p-khdng no doi xung tijr axeton va andehit thorn; tir do da tong hprp dugc 10 hgp chat chua di vdng 2-pirazolin vdi 3 nhdm the. Cau true ctia c^c hgp chit tong hgp dugc xdc nhgn b3ng cac phirofng phap phd IR, NMR, MS va phu hgp vdi
TCHH.T. 50(2), 2012
cdng thirc dy kien. Phd huynh quang ciia cac chat dugc nghien ciru d trang thai ran va cho thay cac hgp chat chira vdng 2-pirazolin d6u phat quang d viing anh sang xanh. Cac nhdm the day hay hiit electron d vj tri 1, 3 va 5 trong vdng 2-pirazolin anh hudng din eye dgi va cudng do phat quang ciia cac hgp chSt nay.
TAI LIEU THAM KHAO
6, 1. Jin Hee Ahn, Hye-Min Kim, Seung Kyu Kang, Jae
Du Ha, Eul Kgun Yum, Duk Keun An, Joong-Kwon Choi, and Sung Soo Kim Bull. Korean Chem, Soc, -j 26(3), 467-469 (2005).
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