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Nguyn nh triu

Cc phng php ph
trong ho hc hu c
v ho sinh

Nh xut bn i hc quc gia h ni

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Mc lc
Li ni u ................................................................................................................. 7
Chng 1. M u ................................................................................................... 10
1.1. Vng ph quang hc...................................................................................... 10
1.2. nh lut Lambert Beer ....................................Error! Bookmark not defined.
1.3. S khi ca ph k quang hc......................Error! Bookmark not defined.
Chng 2. Phng php ph hng ngoi v ph RamanError!
defined.3

Bookmark

not

2.1. Dao ng ca nguyn t trong phn t .............Error! Bookmark not defined.


2.1.1. Tn s dao ng . ...................................Error! Bookmark not defined.
2.1.2. Dao ng chun .....................................Error! Bookmark not defined.
2.1.3. Cc yu t nh hng n tn s c trng.Error!
defined.

Bookmark

not

2.2. Ph hng ngoi ca hirocacbon . ....................Error! Bookmark not defined.


2.2.1. Hirocacbon bo ho..............................Error! Bookmark not defined.
2.2.2. Anken ....................................................Error! Bookmark not defined.
2.2.3. Ankin.....................................................Error! Bookmark not defined.
2.2.4. Hirocacbon thm..................................Error! Bookmark not defined.
2.3. Ancol v phenol. ..............................................Error! Bookmark not defined.
2.4. Ete ...................................................................Error! Bookmark not defined.
2.5. Hp cht anehit v xeton . ..............................Error! Bookmark not defined.
2.6. Axit cacboxylic v dn xut .............................Error! Bookmark not defined.
2.7. Hp cht amin v dn xut . .............................Error! Bookmark not defined.
2.8. Cc hp cht cha nit khc .............................Error! Bookmark not defined.
2.9. Hp cht cha lu hunh, silic v photpho .......Error! Bookmark not defined.
2.10. Hp cht c kim loi ......................................Error! Bookmark not defined.
2.11. Phc cht vi kim loi ....................................Error! Bookmark not defined.
2.12. Ph Raman .....................................................Error! Bookmark not defined.
2.12.1. C s l thuyt .....................................Error! Bookmark not defined.
2.12.2. Ph Raman ca cc hp cht hu c.....Error! Bookmark not defined.

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2.13. Ph k hng ngoi v Raman..........................Error! Bookmark not defined.


2.13.1. Ph k hng ngoi...............................Error! Bookmark not defined.
2.13.2. Ph k Raman ......................................Error! Bookmark not defined.
Chng 3. Phng php ph t ngoi v kh kin ...Error! Bookmark not defined.
3.1. C s l thuyt .................................................Error! Bookmark not defined.
3.1.1. Bc chuyn di nng lng..................Error! Bookmark not defined.
3.1.2. nh lut Lambert Beer..........................Error! Bookmark not defined.
3.1.3. Nhm mang mu ...................................Error! Bookmark not defined.
3.1.4. Phn loi cc di hp th........................Error! Bookmark not defined.
3.1.5. Quy tc la chn trong ph t ngoi kh kin .Error!
defined.

Bookmark

not

3.1.6. Nguyn l Franck - Condon ...................Error! Bookmark not defined.


3.1.7. Cc yu t nh hng n cc i hp th .Error!
defined.

Bookmark

not

3.1.8. Phng php ghi ph .............................Error! Bookmark not defined.


3.2. Ph t ngoi v kh kin ca mt s hp cht hu cError!
defined.

Bookmark

not

3.2.1. Hp cht cha nhm mang mu bit lp.Error! Bookmark not defined.
3.2.2. Hp cht polien......................................Error! Bookmark not defined.
3.2.3. Hp cht polienin v poliin ....................Error! Bookmark not defined.
3.2.4. Hp cht cacbonyl , -khng no C=CC=OError!
defined.

Bookmark

not

3.2.5. Hp cht cha nit .................................Error! Bookmark not defined.


3.2.6. Benzen v dn xut ...............................Error! Bookmark not defined.
3.2.7. H d vng thm ....................................Error! Bookmark not defined.
3.2.8. Axit amin, polipeptit v protein..............Error! Bookmark not defined.
3.3. Phng php phn tch nh lng ...................Error! Bookmark not defined.
3.3.1. Phng php o mt bc sng. ............Error! Bookmark not defined.
3.3.2. Phng php lp ng chun ...............Error! Bookmark not defined.
3.3.3. Tnh hng s phn li...............................Error! Bookmark not defined.
3.4. Cu to ca ph k t ngoi v kh kin. ..........Error! Bookmark not defined.
3.5. Dung mi o ph t ngoi, kh kin .................Error! Bookmark not defined.
Chng 4. Phng php ph cng hng t ht nhnError!
defined.7

Bookmark

not

4.1. Nng lng cng hng ...................................Error! Bookmark not defined.

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4.2. chuyn dch ho hc ...................................Error! Bookmark not defined.


4.2.1. Hng s chn ......................................Error! Bookmark not defined.
4.2.2. Nguyn nhn xut hin hng s chn......Error! Bookmark not defined.
4.2.3. Phng php tnh chuyn dch ho hc..........................................101
4.3. Tng tc spin-spin (xut hin bi nh) ........Error! Bookmark not defined.5
4.3.1. Hng s tng tc spin-spin J.............................................................105
4.3.2. Hng s tng tc geminal, Jgen .........................................................108
4.3.3. Hng s tng tc vicinal, Jvic...........................................................109
4.3.4. Hng s tng tc anlyl, Jal ...............................................................111
4.3.5. Hng s tng tc qua bn lin kt.....................................................111
4.3.6. Hng s tng tc ca proton thm ....................................................112
4.4. Phng php phn tch ph cng hng t ht nhn 1H.Error! Bookmark not
defined.
4.4.1. Cng vch ph ................................Error! Bookmark not defined.
4.4.2. Phn loi ph .........................................Error! Bookmark not defined.
4.5. Phn tch ph cng hng t ht nhn 13C. ......Error! Bookmark not defined.
4.5.1. Ph 13C tng tc 1H..............................Error! Bookmark not defined.
4.5.2. Phng php ph 13C xa tng tc 1H ..Error! Bookmark not defined.
4.5.3. chuyn dch ho hc .........................Error! Bookmark not defined.
4.6. Ph cng hng t ht nhn ca mt s ht nhn khcError! Bookmark not
defined.
4.6.1. Ph CHTNphotpho31 (31P).................Error! Bookmark not defined.
4.6.2. Ph CHTHNflo19 (19F) ......................Error! Bookmark not defined.
4.6.3. Ph CHTHN 14N v 15N ........................Error! Bookmark not defined.
4.7. Mt s phng php h tr phn tch ph cng hng t ht nhn ......... Error!
Bookmark not defined.
4.7.1. Cng hng t kp.................................Error! Bookmark not defined.
4.7.2. Hiu ng NOE .......................................Error! Bookmark not defined.
4.7.3. Tc nhn chuyn dch ho hc................Error! Bookmark not defined.
4.8. Phn tch ph cng hng t ht nhn hai chiu 2DNMR.Error!
not defined.

Bookmark

4.8.1. Ph 2DJ.........................................................................................137
4.8.2. Ph COSY .............................................Error! Bookmark not defined.
4.8.3. Ph HETCOR, HMQC v HSQC. ......Error! Bookmark not defined.9
4.8.4. Ph 2DINADEQUAT. .....................................................................144

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4.8.5. Ph HMBC v COLOC ....................................................................147


4.8.6. Ph TOCSY v HMQC-TOCSY . ......................................................155
4.8.7. Ph NOESY v ROESY.....................................................................159
4.9. Ph cng hng t ht nhn ca mt s hp cht hu c.Error! Bookmark not
defined.
4.9.1. Hp cht bo ho ...............................................................................165
4.9.2. Hp cht loi anken ...........................................................................166
4.9.3. Hp cht ankin...................................................................................167
4.9.4. Benzen v vng ngng t ...................................................................167
4.9.5. Ancol, phenol v ete...........................................................................168
4.9.6. Anehit ..............................................................................................168
4.9.7. Xeton .....................................................Error! Bookmark not defined.
4.9.8. Este, lacton.........................................................................................169
4.9.9. Axit cacboxylic ..................................................................................169
4.9.10. Amin, lactam....................................................................................169
4.9.11. Hp cht cha nhm SH,CSC v C=S .......................................169
4.9.12. Hp cht cha S,O ...........................................................................170
4.9.13. Hp cht cha halogen.........................Error! Bookmark not defined.
4.9.14. Hp cht d vng furan, thiophen, pirol v inol...............................170
4.9.15. Hp cht d vng piriin,quynolin ....................................................171
4.10. Ph cng hng t ht nhn ca axitamin, polipeptit, protein ............... Error!
Bookmark not defined.
4.10.1. Axit amin .............................................Error! Bookmark not defined.
4.10.2. Polipeptit v protein .............................Error! Bookmark not defined.
4.11. Ph k cng hng t ht nhn.......................Error! Bookmark not defined.
4.11.1. Ph k cng hng t ht nhn lin tc (CW-NMR spectrometer)
Error! Bookmark not defined.
4.11.2. Ph k cng hng t ht nhn Fourier ( FT-NMR spectrometer).
Error! Bookmark not defined.
Chng 5. Ph khi ca cc hp cht hu c ........................................................179
5.1. Qu trnh ion ho phn t .............................................................................179
5.1.1. S ion ho..........................................................................................179
5.1.2. Phn loi cc ion. ...............................................................................180
5.1.3. Ph khi phn gii cao .......................................................................184
5.2. C ch phn mnh phn t ...........................................................................186

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5.2.1. C ch tch ankyl (F1)........................................................................186


5.2.2. C ch tch olefin (F2) .......................................................................186
5.2.3. C ch tch anlyl (F3).........................................................................186
5.2.4. C ch tch ion tropylium (F4) ..........................................................187
5.2.5. C ch tch oni (F5) ...........................................................................187
5.2.6. C ch tch Retro-Diels-Alder (F6) ....................................................187
5.2.7. Chuyn v McLafferty (H1) ................................................................187
5.2.8. Chuyn v gc (H2) ............................................................................188
5.2.9. Chuyn v ancol (H3)..........................................................................188
5.2.10. Cng hp Retro (H4) ........................................................................188
5.2.11. Chuyn v Onium (H5) .....................................................................188
5.3. Ph khi ca cc hp cht hu c.................................................................189
5.3.1. Hirocacbon.......................................................................................189
5.3.2. Hp cht ancol, phenol v ete............................................................198
5.3.3. Anehit v xeton ................................................................................209
5.3.4. Axit cacboxylic ..................................................................................214
5.3.5. Amin..................................................................................................220
5.3.6. Cc hp cht cha nit khc...............................................................224
5.3.7. Hp cht azo, azometin v oxim ........................................................227
5.3.8. Hp cht halogen v thio....................................................................228
5.3.9. Hp cht d vng................................................................................233
5.3.10. Ph khi ca mt s ancaloit d vng . .............................................241
5.3.11. Ph khi ca axit amin v polipeptit.................................................244
5.4. Nguyn l cu to khi ph k ......................................................................248
5.4.1. Ho kh mu.......................................................................................248
5.4.2. Ion ho mu .......................................................................................249
5.4.3. Tch cc ion theo s khi ...................................................................250
5.4.4. etect ..............................................................................................253
5.4.5. Ghi nhn tn hiu................................................................................253
5.4.6. S cu to khi ph k ..................................................................253
Chng 6. Phn bi tp ..........................................................................................263
6.1. Bi tp ph hng ngoi .................................................................................263
6.2. Bi tp ph t ngoi .....................................................................................269
6.3. Bi tp ph cng hng t ht nhn..............................................................274

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6.4. Bi tp ph khi lng .................................................................................287


6.5. Bi tp tng hp ...........................................................................................292
Ti liu tham kho ..................................................................................................323

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LI NI U
Ngy nay ha hc hu c ang pht trin mnh m c l thuyt v ng dng,
hng nm c hng vn cht mi c tng hp hoc tch t thin nhin ra do yu
cu tch tinh khit v xc minh cu to ca chng l rt cn thit, n i hi phi nhanh
v chnh xc. Xa kia chng minh cu to mt cht c th mt hng nm hoc c khi
ko di c chc nm th nay c th thc hin c sau vi gi, s d lm c nh vy
l nh c cc phng php vt l hin i h tr nh cc phng php sc k v cc
phng php ph. V th s hiu bit v cc phng php vt l ni chung v phng
php ph ni ring l rt cn thit cho tt c nhng ai hc tp v nghin cu ha hc
hu c v ha sinh.
Ni dung ca cun sch ny khng i su v l thuyt cc phng php ph m
tp trung vo phn ng dng cc phng php ph hng ngoi, ph t ngoi v kh
kin, ph cng hng t ht nhn 1H v 13C v ph khi lng phn tch cu trc cc
hp cht hu c, trong cun sch ny cn c a vo mt lng bi tp ng k gip
cho ngi c c th t mnh c c cc ph v gii thch cu to ca hp cht.
Cun sch ny c th dng lm ti liu hc tp v tham kho cho sinh vin, hc
vin cao hc, nghin cu sinh v cn b ngnh ha hu c v ha sinh ca cc trng
i hc v Vin nghin cu.
H Ni, ngy 30 thng 8 nm 2007
Tc gi

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Chng 1

M U
phn tch cu to cc hp cht hu c c th s dng cc phng php ph
nh ph hng ngoi, ph t ngoi v kh kin, ph cng hng t ht nhn, ph khi
lng. Mi phng php cho php xc nh mt s thng tin khc nhau ca cu to
phn t, nh phng php ph hng ngoi cho php xc nh s c mt ca cc nhm
chc trong phn t nh nhm OH, NH, CH, C=C, CC, C=O, C=N, N=N..; phng
php ph t ngoi, kh kin cho php xc nh hp cht l h ni i lin hp, h
vng thm hay vng bo ho; phng php ph cng hng t ht nhn cho php
xc nh cu trc khng gian ca phn t v phng php ph khi lng cho php xc
nh chnh xc khi lng phn t, t l phn trm ca cc nguyn t C, S, Br, Clv
chng minh cu to phn t.
C s ca cc phng php ph hng ngoi, Raman, t ngoi v kh kin gi
chung l phng php quang ph l s tng tc ca nh sng vi phn t.

1.1. Vng ph quang hc


Khi cc phn t tng tc vi cc vng nh sng s hp th nng lng ca nh
sng v xy ra cc qu trnh khc nhau nh quay phn t, dao ng nguyn t trong
phn t v kch thch cc electron lin kt, cho cc loi ph khc nhau nh ph quay,
ph hng ngoi v ph t ngoi (bng 1.1). Vng nh sng c bc sng t 50 nm
n 200 nm (ph t ngoi chn khng, UV vacum) t 200 n 400 nm (ph t ngoi,
UV), t 400 n 800 nm (ph kh kin, VIS) v t 0,8 n 50 m (ph hng ngoi, IR)
c gi l vng ph quang hc. Ngoi ra, vng t 50 n 800 nm cn c tn gi l ph
in t (hay ph electron) bao gm ph t ngoi chn khng, t ngoi v kh kin.

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