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c th phn loi v hiu ng cm, ngi ta quy c chn nguyn t hydrogen so snh (Ni
C H c xem nh khng phn cc: I = 0)
v
Nguyn t hay nhm nguyn t c khuynh hng y in t (ht in t yu hn
hydrogen) gy hiu ng cm dng (+I).
v
Ch lin quan n in t ca ni n .
b2. Cc nhm c nguyn t mang in tch m nh oxid, sulfur... cho in t tng i d dng:
nh vy, gy hiu ng + I mnh. V S - c kch thc ln hn O -, in t t b nhn ht hn, nn
d nhng hn.
b.
Nh vy, mun bit hiu ng cm chung ca mt nhm phc tp, ngi ta cng i s
cc hiu ng ca cc thnh phn ca n.
Bng 1.1. HIU NG CM TNG I CA CC NHM THNG THNG
HIU NG - I
HIU NG + I
Ghi ch Me : CH3
1.7. ng dng
Acid cng mnh khi: Ka cng ln ([H+] cng ln), hay pKa cng nh: c ngha l khi nh lin
ha tr gia O v H cng b ko v pha O, cng lm gia tng s phn cc ca lin kt O - H:
khi ,H cng d tch ri thnh ion H+.. Do :
Ngc li, khi phn t acid c nhm gy hiu ng cm dng, mnh acid s gim.
TN THNG THNG
CNG THC CU TO
pKa
Acid formic
HCOOH
3,75
Acid acetic
CH3COOH
4,75
Acid monocloroacetic
ClCH2COOH
2,81
Acid butanoic
CH3CH2CH2COOH
4,82
Acid a-clorobutanoic
CH3CH2CHClCOOH
2,9
Acid b-clorobutanoic
CH3CHClCH2COOH
4,1
Acid g-clorobutanoic
CH2ClCH2CH2COOH
4,5
Khi phn t baz c nhm gy hiu ng cm dng (+ I), mnh ca baz s tng.
2.
b.
Vn o p trng: l vn o p khng c in t
Hai c cu cng hng (I) v (II) trn ca acid acetic c cng s ni cng ha tr, nhng c cu (II)
t bn hn v c s phn ly in tch . Acid acetic ging dng (I) nhiu hn dng (II).
f. S phn cch in tch cng du cng ln, c cu cng hng cng bn. V tri li, s phn
cch in tch khc du cng ln, c cu cng hng cng t bn.
Cng thc cng hng vi 2 in tch cng du trn 2 nguyn t k cn khng bn. Do ,
dng ny khng c trong thc t.
HIU NG - R
HIU NG +R
HIU NG - R
HIU NG +R
2.7. ng dng
Hiu ng cng hng cng c nhng ng dng tng t nh hiu ng cm
a. Gii thch mnh ca cc acid hu c
Cc cht hu c c cha nhm -OH c th phng thch proton H+, do c tnh acid.
Acid cng mnh khi: Ka cng ln ([H+] cng ln), hay pKa cng nh: c ngha l khi nh
lin ha tr gia O v H cng b ko v pha O, cng lm gia tng s phn cc ca lin kt O H:
khi ,H cng d tch ri thnh ion H+.. Do :
Khi acid c nhm gy hiu ng cng hng m (-R) lm cho nh lin ca --OH b ko v gn O
hn, mnh acid s tng.
Ngc li, khi phn t acid c nhm gy hiu ng cng hng dng (+R) lm cho nh lin ca
--OH t b ko v O hn, mnh acid s gim.
Th d @1: So snh tnh acid ca etanol v phenol: ta thy tnh acid ca phenol mnh hn tnh
acid ca etanol (pKa ca phenol = 10 ; trong khi pKa ca etanol = 17)
GII THCH
Trong phn t etanol, nhm etil gy hiu ng + I, y in t v nhm -OH, lm gim s phn cc
ca lin kt gia O v H.
Trong phn t phenol, do hiu ng cng hng p - p , i in t p t do ca oxigen di chuyn v
pha nhn benzen: lm nhn benzen cng di do in t c bit cc v tr orto v para, O tr
nn thiu in t, cng c khuynh hng ko i in t gp chung vi H v pha n, lm tng s
phn cc ca lin kt O-H. Do , phenol c tnh acid mnh hn etanol.
Th d @2. So snh tnh acid ca p-nitrophenol v m-nitrophenol, ngi ta nhn thy pnitrophenol (pKa = 7,15) c tnh acid mnh hn m-nitrophenol.
GII THCH
C 2 acid u c nhm -NO2 gy ra hiu ng -R v -I, c tc dng rt in t mnh. Tuy nhin, vi
phn t p-nitrophenol, hiu ng cng hng lan rng n nguyn t O ca nhm -OH, mt in
t trn O gim: cng lm nh lin ha tr gia O v H b ko v pha O, H d tch ri di dng
H+ .
Tri li, trong phn t m-nitrophenol, hiu ng cng hng m do nhm -NO2 gy ra ch
lin h n nhn benzen v khng truyn ti nhm -OH. Do , lin kt O-H kh t hn v mnitrophenol c tnh acid yu hn p-nitrophenol.