spektroskopi ultraviolet visibel
TRANSCRIPT
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SPEKTROSKOPI ULTRAVIOLET (UV)SPEKTROSKOPI ULTRAVIOLET (UV)
Oleh:Prof. Dr. Suyatno, MSi
Program Studi Pendidikan SainsProgram Pascasarjana
Universitas Negeri Surabaya2011
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SPEKTROSKOPI ULTRAVIOLET (UV)SPEKTROSKOPI ULTRAVIOLET (UV)[[λ : 100-190 (UV Vakum), 190-400 (UV Dekat)]
TRANSISI ELEKTRON ANTAR TINGKAT ENERGI ELEKTRONIK (n)
σ → σ* (λmaks < 200 nm)π → π* (λmaks: 200-700 nm)n → σ* (λmaks: 150-250 nm)n → π* (λmaks: 200-700 nm)
GUGUS KROMOFOR SUATU SENYAWA ORGANIK
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GUGUS KROMOFOR
MENGABSORBSI ENERGI RADIASI ULTRAVIOLET
DIENA TERKONJUGASI DAN TAK TERKONJUGASITRIENA TERKONJUGASI DAN TAK TERKONJUGASIKOMBINASI DIENA DAN TRIENAKETONKETON TAK JENUH TERKONJUGASI DAN TAK TERKONJUGASIDAN LAIN-LAIN
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ISTILAH PENTING DALAM SPEKTROSKOPI UV
GUGUS KROMOFORGUGUS AUKSOKROM
PERGESERAN MERAH (BATOKROMIK/ RED SHIFT)PERGESERAN BIRU (HIPSOKROMIK/ BLUE SHIFT)
EFEK HIPOKROMEFEK HIPERKROM
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CARA MEMPREDIKSI PANJANG GELOMBANG MAKSIMUM (λ maks) SERAPAN UV
SUATU SENYAWA ORGANIK
ATURAN WOODWARD
DIENA TERKONJUGASI ENON
BENZENA TERSUBSTITUSI
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ATURAN WOODWARDDIENA TERKONJUGASI
HARGA λ maks DASAR:1. DIENA ASIKLIK DAN HETEROANULAR ………………215 nm2. DIENA HOMOANULAR……………………………………253 nm
PENAMBAHAN SETIAP SUBSTITUEN:1. – R (ALKIL) …………+ 5 nm2. – OR (ALKOKSI)……………+6 nm3. – SR (TIOFEN)……………………...+30 nm4. – Cl, Br……………………………………...+5 nm5. – OCOR ………………………………………....+0 nm6. PERPANJANGAN –CH=CH-……………………..+30 nm7. IKATAN RANGKAP EKSOSIKLIK………………………+5 nm
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LATIHAN
CH2
CH2(a)
H3C CH3
(b) (c)
(d) (e)AcO
(f)AcO
(g)HO
(h)
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CONTOH SPEKTRUM UV
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ATURAN WOODWARDENON
HARGA λ maks DASAR:1. KETON TAK JENUH α,β ASIKLIK DAN SIKLIK 6 ANGGOTA…215 nm2. KETON TAK JENUH α,β SIKLIK 5 ANGGOTA …………………..202 nm3. ALDEHID TAK JENUH α,β …………………………………………..207 nm4. ASAM DAN ESTER TAK JENUH α,β ………………………………..195 nm
PENAMBAHAN SETIAP SUBSTITUEN:1. – R (ALKIL) ………………………+ 10 (α), 12 (β), 18 (γ ), 18 (δ) nm2. – OR ……………………………….+ 35 (α ), 30 (β ), 17 (γ ), 30 (δ) nm3. – SR…………………………………+ 85 (β) nm4. – OH…………………………….....+35 (α ), 30 (β ), - (γ), 50 (δ) nm5. – Cl………………………….....…...+ 15 (α), 12 (β) nm6. – Br…………………………….…...+25 (α), 30 (β) nm7. – OCOR , -OCOAr…………..……+ 6 (α, β, γ, δ ) nm8. – NR2…………………………...….+95 (β) nm9. PERPANJANGAN –CH=CH-……………………….……..+30 nm10. IKATAN RANGKAP EKSOSIKLIK………………………+5 nm11. DIENA HOMOANULAR………………………………….+ 39 nm
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LATIHAN
H3C
H3C
O
CH3
(a)
H3C
H3C
O
CH3OH
(b)
O
OCH3(c)
O
OH
OCH3
(d)
O
OH
(e)
H3CO
O
OC2H5
(f)
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ATURAN FIESER-KUHNPOLIENA
λ maks = 114 + 5 M + n (48 – 1,7 n) – 16,5 Rendo – 10 Rexo nmε Maks = (1,74 X 104) n
n = Jumlah ikatan rangkap terkonjugasiM = Jumlah gugus alkil atau serupa alkil pada sistem
terkonjugasiR endo = Jumlah cincin dengan ikatan rangkap endosiklik dalam
sistem terkonjugasiR exo = Jumlah cincin dengan ikatan rangkap exosiklik dalam
sistem terkonjugasi
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EXERCISES
O
HO
O
OH
(a)
O
CH3
HO
(b)
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EXERCISES
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EXERCISES
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SENYAWA TURUNAN BENZENA TERSUBSTITUSI
HARGA λ maks DASAR KROMOFOR INDUK:1. Z = R ATAU SISA LINGKAR …………………………………….....246 nm2. Z = H ……………………………………………………………………..250 nm3. Z = OH ATAU OR …………………………….………………………..230 nm
PENAMBAHAN SETIAP SUBSTITUEN:orto meta para
1. – ALKIL/SISA LINGKAR…………… 3 3 102. – OH,OR ………………………………. 7 7 253. – O………………………………………11 20 784. – Cl………………………….....……….. - - 105. – Br…………………………….……….. 2 2 15 6. – NH2………………………...……..…..13 13 588. – NHAc….…………………………...…20 20 459. –NHMe…………………………….…….- - 7310. –NMe2…………….……………………20 20 85
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LATIHAN
(a)
O
OC2H5
H2N
OCH3
(b)
O
OH
H3CO
O(c)
O(d)
Cl CH3 O
OC2H5
(e)O
H3CO
OCH3