Stereoelectronic Effect
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- ただきよ よどぎみ
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2 node anti bonding M ( σ* ) A A : bonding M ( σ ) A: atomic orbital M: molecular orbital
3 node anti bonding M filled orbital of molecular 1 M bonding M vacant orbital of molecular 2 LUM
4 LUM (lowest unoccupied molecular orbital) 3 3 anti bonding σ* x bonding π' z π' y σ x M (highest occupied molecular orbital) z π z π y σ 's y x σ s
5 3 3 LUM Eσ * σ* x Eσ σ x p x p x M
6 2 2 π* z LUM anti bonding bonding π z M π' y π y π x z σ' s y σ s x
7 2 2 LUM Eπ * π* Eπ π p z p z M
8 LUM σ* x Eσ * p x Eσ σ x p x M
9 LUM Eσ * π* Eσ p x π p x M
10 Ψ 4 π* π* Ψ 3 anti bonding LUM bonding M Ψ 2 π π Ψ 1
11
12 LUM (1) M (1) LUM (2) M (2)
13 Nu (M) π* = (LUM) π = (M) E (LUM)
14 p orbital axis N M LUM θ axis θ = 109 ( Bürgi-Dunitz angle) M N LUM l axis
15 M-LUM M-LUM Na + LUM M l - M δ + δ - 2 Br Br 2 LUM
16 Ψ 1 Ψ 2 hard soft +, + = 3 Si +
17 cyclooctene trans cis π bond biradical θ θ θ = 0 θ =
18 Bredtʼs rule: (bridgehead) Ph N Me Bz Ac taxol Ac P-263,114 2
19 2 M π ' ' ' ' σ SP 3 ( ' ' SP 2
20 1) rotation about single bond ' ' ' synclinal ' antiperiplaner ' < << ' eclipsed gauche staggered (anti) ' E a eclipsed σ - E b σ - Ea + Eb = 0 rule:two-electron interactions are bonding, four-electron interactions are antibonding.
21 ' 3 1,3-diaxial interaction ' 2 1 cis 1 3 ' 1 ' 3 allylic 1,3-strain (A strain) ' 30 '
22 1,3-diaxial interaction ' ' eq eq α-d-glucose β-d-glucose 1-methyl derivative ax 1,3-diaxial interaction 2 64% eq Me 2 67% 33% Me 36% pentacetyl derivative tetracetyl 1-chloro derivative Ac Ac Ac Ac Ac 2 Ac Ac Ac Ac 86% 14% Ac Ac Ac Ac Ac l 2 Ac Ac Ac 94% 6% Ac l ax electronegative group
23 σ-delocalisation n-σ* overlap effect anomeric effect n (M) σ* - (LUM) n antiperiplanar σ* - rule: There is a stereoelectronic preference for conformations in which the best donor lone pair is antiperiplanar to the best acceptor bond. antiperiplanar
24 σ σ σ (M) σ* - (LUM) ' staggered (anti) antiperiplanar rule: There is a stereoelectronic preference for conformations in which the best donor σ bond is antiperiplanar to the best acceptor bond. M: n N > n > σ -, σ - >> σ -N > σ - > σ -S > σ -hal LUM: π* = > σ* -hal > σ* - > σ* -N > σ* -, σ* -
25 F F staggered (anti) repulsion? F F gauche F F σ - -σ* -F interaction σ (M) F σ* -F (LUM)
26 Karplis 3 J 1,2 θ θ θ 0 θ = 0 θ = 90 θ = 180 σ - (M) σ* - (LUM) σ - (M) σ* - (LUM)
27 I. 1) S N 1 reaction of haloalkane cation 3 cation << 3 << 3 hyperconjugation 3? σ (M) vacant P (LUM)
28 α Me l Me l - Me hyperconjugation n (M) vacant P (LUM)
29 3) reactivity and regioselectivity for the Friedel-rafts reaction Me Me Me - Me Me o p hyperconjugation n (M) Me vacant P (LUM) Ac
30 σ-σ* interaction short F long NMe 3 F S + NMe 3 F NMe 3 trifluoromethoxide F F F F n -σ* -F hyperconjugation σ* -F (LUM) F F F n (M)
31 ' N 3 3 N ' N n N σ* - axis N ' ' - - N ' N ' N '
32 S Me S Me S S Me Me S 2 Ar S 2 Ar S 2 Ar S 2 Ar Ar 2 S S Me Ar 2 S S
33 exo endo Y 6-exo-tet Y 6-endo-tet θ θ = 180 tet (SP 3 ) θ = 109 θ trig (SP 2 ) θ = 60 θ trig (SP 2 )
34 Me N 5-endo-trig Me endo N 2 exo Me N 2 5-exo-trig N Me 2 Me 3 Na Ph 5-endo-dig Ph Ph
35 (1) (2) n l σ* -l l fast Br fast slow Br Br twist boat chair (1) (2) a b Br Br chair Br endo exo a b 6-endo-tet 5-exo-tet exo? twist boat
36 S N 2 (1) M/LUM M Y LUM Y π = (M) π = (LUM) Y Y Y Y n (M) Me 2 NPh Br N + Me 2 Ph Y Y Br N + Me 100 times faster!! 2 Ph
37 S N 2 (2) S + NS S NS Bn S + Bn S NS NS S + NS S NS-Et 8000 times slower!! S + S + NS NS
38 S N 1 (1) π = n S N 1 S N 2 π = n π = vacant
39 S N 1 (2) σ =,, metal ( σ delocalization σ p
40 Si E + Si E E Si E a Si E Si E + a b E + b Si E
41 σ-delocalisation Involving - bond (1) σ - σ cyclopropane cyclopropane π* = π* = cf.
42 σ-delocalisation Involving - bond (2) a l 2 a a b b b
43 σ-delocalisation Involving - bond throuh the space the center of electron-density 2 N
44 MgBr 2 2 M MgBr LUM σ -M (M) M Br σ* Br-Br (LUM) Br
45 (t-bu 2 ) 3 Sn Et Me Br 2 Br Et Me Et Me Br retention inversion σ -M (M) Sn Br σ* Br-Br (LUM) Br σ -M (M) Sn Br Br σ* Br-Br (LUM) retention inversion
46 1) (1) Nu Nu Nu M Nu Nu π* = (LUM) Nu 1 2 Nu β-attack α-attack β α Nu * 2 1 * 2 Nu 1
47 (1) t-bu t-bu t-bu α- β- Li(sec-Bu) 3 B 97 : 3 NaB 4 14 : 86 bulky t-bu 1,3-diaxial interaction
48 α σ Nu β-attack? α-attack σ* - (LUM) Nu α-attack? Nu Nu M ram (Felkin-Anh ) Nu S 109 M L Felkin-Anh model Nu S L L S Nu M chlation model
49 Nu Nu Nu β-attack twist boat + Nu α-attack Nu Nu chair
50 -Y Y σ* Br-Br (LUM) Br Br Br Br Br Br Br Br π = (M) Br Br σ* - (LUM) + π = (M)
51 Y + Y M n π = σ - p σ -Si Si
52 π Z -Y Z Y Z β-face π = (M) E α-face σ -Z Z Z: electron donating group Z 1 2 -Y Z * * 2 1 Y 1 2 Z Allylic 1,3-strain β-face 1 2 Z 30 1,2-strain 2 1 Z Z
53 π t-bu trans SiMe 3 Ph t-bul, Til Me Ph 4 Me Ph t-bu σ -Si Si cis SiMe 3 Ph t-bu t-bul, Til S Ph 4 Ph t-bu Me σ -Si Me Si
54 π emote ontrol by F atom F σ - σ* - "" mpba F F ( 2 : 1 ) Z-isomer E-isomer
55 Me S Me S Me S Me S Me S σ* -S S S S Me S S Z-enolate Z-enolate Me S σ* -S 1,4-addition Me S Me S "syn-isomer" π π
56 β Elimination 1) E1 - + cation intermadiate 2) E2 B - B + 3) E1cB B B + -
57 2) E2 - + σ - (M) vacant P (LUM) σ - (M) - σ* - (LUM) B + NMe 3 NMe 3 NMe 3 NMe 3 anti: 95% Me 3 N NMe3 anti : syn = 54 : 46 σ - (M) σ* - (LUM) syn: 90% synperiplaner
58 NMe 3 NMe 2 92% 8% Me N Me Me S N 2 100% NMe 2
59 Me Me Br Br σ σ* σ σ* σ σ* σ σ* Sp 3 anti Sp 3 syn Sp 2 anti Sp 2 syn
60 2 2 Ms tert-bu Ms
61 N N 2 / N Ts N l N 2 N N Me Ts N Me
62 1,2-shift σ 1 2 σ* antiperiplaner Pinacol earrangement 2 antiperiplaner antiperiplaner
63 Beckman earrangement Ar σ Me N Me N σ* Ts Ar 2 Me N Ar antiperiplaner ofman earrangement Ar N NaBr Na Ar σ N σ* Br N Ar 2 N Ar antiperiplaner
64 σ σ LUM: π* = > σ* -hal > σ* - > σ* -N n (M) σ* - (LUM) σ (M) σ* - (LUM) antiperiplanar
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24 I ( ) 1. R 3 (i) C : x 2 + y 2 1 = 0 (ii) C : y = ± 1 x 2 ( 1 x 1) (iii) C : x = cos t, y = sin t (0 t 2π) 1.1. γ : [a, b] R n ; t γ(t) = (x
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24 I 1.1.. ( ) 1. R 3 (i) C : x 2 + y 2 1 = 0 (ii) C : y = ± 1 x 2 ( 1 x 1) (iii) C : x = cos t, y = sin t (0 t 2π) 1.1. γ : [a, b] R n ; t γ(t) = (x 1 (t), x 2 (t),, x n (t)) ( ) ( ), γ : (i) x 1 (t),
128 3 II S 1, S 2 Φ 1, Φ 2 Φ 1 = { B( r) n( r)}ds S 1 Φ 2 = { B( r) n( r)}ds (3.3) S 2 S S 1 +S 2 { B( r) n( r)}ds = 0 (3.4) S 1, S 2 { B( r) n( r)}ds
127 3 II 3.1 3.1.1 Φ(t) ϕ em = dφ dt (3.1) B( r) Φ = { B( r) n( r)}ds (3.2) S S n( r) Φ 128 3 II S 1, S 2 Φ 1, Φ 2 Φ 1 = { B( r) n( r)}ds S 1 Φ 2 = { B( r) n( r)}ds (3.3) S 2 S S 1 +S 2 { B( r) n( r)}ds
09 II 09/12/ (3D ) f(, y) = 2 + y 2 3D- 1 f(0, 0) = 2 f(1, 0) = 3 f(0, 1) = 4 f(1, 1) = 5 f( 1, 2) = 6 f(0, 1) = z y (3D ) f(, y) = 2 + y
09 II 09/12/21 1 1 7 1.1 I 2D II 3D f() = 3 6 2 + 9 2 f(, y) = 2 2 + 2y + y 2 6 4y f(1) = 1 3 6 1 2 9 1 2 = 2 y = f() f(3, 2) = 2 3 2 + 2 3 2 + 2 2 6 3 4 2 = 8 z = f(, y) y 2 1 z 8 3 2 y 1 ( y ) 1 (0,
4 Mindlin -Reissner 4 δ T T T εσdω= δ ubdω+ δ utd Γ Ω Ω Γ T εσ (1.1) ε σ u b t 3 σ ε. u T T T = = = { σx σ y σ z τxy τ yz τzx} { εx εy εz γ xy γ yz γ
Mindlin -Rissnr δ εσd δ ubd+ δ utd Γ Γ εσ (.) ε σ u b t σ ε. u { σ σ σ z τ τ z τz} { ε ε εz γ γ z γ z} { u u uz} { b b bz} b t { t t tz}. ε u u u u z u u u z u u z ε + + + (.) z z z (.) u u NU (.) N U
8. 置換基の電子的性質 誘起効果と共鳴効果 誘起効果 Inductive Effect (I 効果 ) σ 結合を通じて伝わる極性結合と隣の結合との相互作用 電気陰性度の差が重要 1) 陰性の原子 ( 置換基 ) による場合 (-I 効果 ) δδδ+ C δδ+ C δ+ C
8. 置換基の電子的性質 誘起効果と共鳴効果 8-1 8.1. 誘起効果 Inductive Effect (I 効果 ) σ 結合を通じて伝わる極性結合と隣の結合との相互作用 電気陰性度の差が重要 1) 陰性の原子 ( 置換基 ) による場合 (-I 効果 ) X X X: alogen,, R, R 2, R, 2... 電気陰性度大 :-I 効果大 2) 陽性の置換基による場合 (Li, B,
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1 1 1.1 64 A6, 1) B1, 1) 65 C A, 1) B, ) C 66 + 1 = 0 A1, 1) B, 0) P 67 A, ) B1, ) C4, 0) 1) ABC G ) A B C P 64 A 1, 1) B, ) AB AB = 1) + 1) A 1, 1) 1 B, ) 1 65 66 65 C0, k) 66 1 p, p) 1 1 A B AB A 67
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寄稿論文 ボロンアルドール反応の新展開 | 東京化成工業
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医系の統計入門第 2 版 サンプルページ この本の定価 判型などは, 以下の URL からご覧いただけます. このサンプルページの内容は, 第 2 版 1 刷発行時のものです.
医系の統計入門第 2 版 サンプルページ この本の定価 判型などは, 以下の URL からご覧いただけます. http://www.morikita.co.jp/books/mid/009192 このサンプルページの内容は, 第 2 版 1 刷発行時のものです. i 2 t 1. 2. 3 2 3. 6 4. 7 5. n 2 ν 6. 2 7. 2003 ii 2 2013 10 iii 1987
SO(3) 7 = = 1 ( r ) + 1 r r r r ( l ) (5.17) l = 1 ( sin θ ) + sin θ θ θ ϕ (5.18) χ(r)ψ(θ, ϕ) l ψ = αψ (5.19) l 1 = i(sin ϕ θ l = i( cos ϕ θ l 3 = i ϕ
SO(3) 71 5.7 5.7.1 1 ħ L k l k l k = iϵ kij x i j (5.117) l k SO(3) l z l ± = l 1 ± il = i(y z z y ) ± (z x x z ) = ( x iy) z ± z( x ± i y ) = X ± z ± z (5.118) l z = i(x y y x ) = 1 [(x + iy)( x i y )
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Contents a 6 6 6 6 6 6 6 7 7. 8.. 8.. 8.3. 8 Part. 9. 9.. 9.. 3. 3.. 3.. 3 4. 5 4.. 5 4.. 9 4.3. 3 Part. 6 5. () 6 5.. () 7 5.. 9 5.3. Γ 3 6. 3 6.. 3 6.. 3 6.3. 33 Part 3. 34 7. 34 7.. 34 7.. 34 8. 35
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1 1 1.1 I R 1.1.1 c : I R 2 (i) c C (ii) t I c (t) (0, 0) c (t) c(i) c c(t) 1.1.2 (1) (2) (3) (1) r > 0 c : R R 2 : t (r cos t, r sin t) (2) C f : I R c : I R 2 : t (t, f(t)) (3) y = x c : R R 2 : t (t,
28 Horizontal angle correction using straight line detection in an equirectangular image
28 Horizontal angle correction using straight line detection in an equirectangular image 1170283 2017 3 1 2 i Abstract Horizontal angle correction using straight line detection in an equirectangular image
4. ϵ(ν, T ) = c 4 u(ν, T ) ϵ(ν, T ) T ν π4 Planck dx = 0 e x 1 15 U(T ) x 3 U(T ) = σt 4 Stefan-Boltzmann σ 2π5 k 4 15c 2 h 3 = W m 2 K 4 5.
A 1. Boltzmann Planck u(ν, T )dν = 8πh ν 3 c 3 kt 1 dν h 6.63 10 34 J s Planck k 1.38 10 23 J K 1 Boltzmann u(ν, T ) T ν e hν c = 3 10 8 m s 1 2. Planck λ = c/ν Rayleigh-Jeans u(ν, T )dν = 8πν2 kt dν c
19 σ = P/A o σ B Maximum tensile strength σ % 0.2% proof stress σ EL Elastic limit Work hardening coefficient failure necking σ PL Proportional
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