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1 Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004 Chem. Eur. J Supporting Information for
2 Chem. Eur. J. Supporting Information For Quantitative Evaluation of d-p Interaction in Copper(I) Complexes and Control of Copper(I)-Dioxygen Reactivity Takao Osako, Yoshimitsu Tachi, Matsumi Doe, Motoo Shiro, Kei Ohkubo, Shunichi Fukuzumi, * and Shinobu Itoh * 1
3 Figure S1 C40 C39 C38 C41 C42 C43 C44 C37 C30 N6 Cu2 C36 N4 C29 C31 C34 C35 N5 C27 C28 C32 C33 C23 C26 C24 C25 Figure S1. ORTEP diagram of [Cu I (L1 H )]ClO 4 (1 H ) (molecule 2) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 2
4 Figure S1 Figure S1. ORTEP diagram of [Cu I (L1 H )]ClO 4 (1 H ) with thermal ellipsoids at 50 % probability. Crystallographically independent ten molecules are involved in a unit cell. 3
5 Table S1. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 H )]ClO 4 (1 H ). Molecule 1 Molecule 2 Cu(1)-N(1) 2.083(3) Cu(2)-N(4) 2.107(4) Cu(1)-N(3) 2.003(3) Cu(2)-N(5) 1.998(3) Cu(1)-N(2) 2.018(4) Cu(2)-N(6) 2.011(4) Cu(1)-C(17) 2.326(4) Cu(2)-C(39) 2.257(4) Cu(1)-C(22) 2.247(4) Cu(2)-C(44) 2.217(4) C(17)-C(22) 1.411(6) C(39)-C(40) 1.399(7) C(17)-C(18) 1.408(6) C(39)-C(44) 1.410(7) C(18)-C(19) 1.376(7) C(40)-C(41) 1.378(8) C(19)-C(20) 1.394(7) C(41)-C(42) 1.390(7) C(20)-C(21) 1.381(7) C(42)-C(43) 1.368(7) C(21)-C(22) 1.398(7) C(43)-C(44) 1.401(6) N(1)-Cu(1)-N(3) 102.0(1) N(4)-Cu(2)-N(5) 99.9(1) N(1)-Cu(1)-N(2) 102.5(1) N(4)-Cu(2)-N(6) 102.2(1) N(2)-Cu(1)-N(3) 110.0(1) N(5)-Cu(2)-N(6) 108.6(1) N(1)-Cu(1)-C(17) 84.2(1) N(4)-Cu(2)-C(39) 86.0(2) N(3)-Cu(1)-C(17) 119.3(1) N(5)-Cu(2)-C(39) 140.1(2) N(2)-Cu(1)-C(17) 127.7(1) N(6)-Cu(2)-C(39) 108.5(2) N(1)-Cu(1)-C(22) 111.1(1) N(4)-Cu(2)-C(44) 100.1(2) N(3)-Cu(1)-C(22) 130.8(1) N(5)-Cu(2)-C(44) 103.9(2) N(2)-Cu(1)-C(22) 97.5(1) N(6)-Cu(2)-C(44) 136.3(2) C(17)-Cu(1)-C(22) 35.9.(2) C(39)-Cu(2)-C(44) 36.7(2) 4
6 Table S1. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 H )]ClO 4 (1 H ) (continued). Molecule 3 Molecule 4 Cu(3)-N(7) 2.080(4) Cu(4)-N(10) 2.101(3) Cu(3)-N(8) 2.015(3) Cu(4)-N(12) 2.005(3) Cu(3)-N(9) 1.992(3) Cu(4)-N(11) 1.999(4) Cu(3)-C(61) 2.325(3) Cu(4)-C(83) 2.395(4) Cu(3)-C(66) 2.230(4) Cu(4)-C(84) 2.187(4) C(61)-C(62) 1.398(6) C(83)-C(88) 1.409(6) C(61)-C(66) 1.423(7) C(83)-C(84) 1.418(6) C(62)-C(63) 1.374(7) C(88)-C(87) 1.370(6) C(63)-C(64) 1.397(7) C(87)-C(86) 1.392(7) C(64)-C(65) 1.370(7) C(86)-C(85) 1.390(7) C(65)-C(66) 1.387(7) C(85)-C(84) 1.403(7) N(7)-Cu(3)-N(8) 102.8(1) N(10)-Cu(4)-N(12) 102.5(1) N(7)-Cu(3)-N(9) 102.3(1) N(10)-Cu(4)-N(11) 102.5(1) N(8)-Cu(3)-N(9) 111.8(1) N(11)-Cu(4)-N(12) 111.7(1) N(7)-Cu(3)-C(61) 84.5(1) N(10)-Cu(4)-C(83) 81.7(1) N(8)-Cu(3)-C(61) 130.0(1) N(12)-Cu(4)-C(83) 141.0(1) N(9)-Cu(3)-C(61) 114.6(1) N(11)-Cu(4)-C(83) 104.8(1) N(7)-Cu(3)-C(66) 114.0(2) N(10)-Cu(4)-C(84) 100.3(2) N(8)-Cu(3)-C(66) 101.6(2) N(12)-Cu(4)-C(84) 106.5(2) N(9)-Cu(3)-C(66) 122.9(2) N(11)-Cu(4)-C(84) 129.4(2) C(61)-Cu(3)-C(66) 36.2(2) C(83)-Cu(4)-C(84) 36.0(2) 5
7 Table S1. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 H )]ClO 4 (1 H ) (continued). Molecule 5 Molecule 6 Cu(5)-N(13) 2.075(3) Cu(6)-N(16) 2.098(3) Cu(5)-N(14) 1.992(3) Cu(6)-N(17) 2.001(3) Cu(5)-N(15) 2.012(3) Cu(6)-N(18) 2.005(3) Cu(5)-C(105) 2.322(4) Cu(6)-C(127) 2.379(4) Cu(5)-C(106) 2.212(4) Cu(6)-C(128) 2.186(4) C(105)-C(106) 1.414(6) C(127)-C(128) 1.398(6) C(105)-C(110) 1.418(6) C(127)-C(132) 1.404(6) C(106)-C(107) 1.401(7) C(128)-C(129) 1.399(6) C(107)-C(108) 1.376(7) C(129)-C(130) 1.387(6) C(108)-C(109) 1.381(6) C(130)-C(131) 1.386(6) C(109)-C(110) 1.370(6) C(131)-C(132) 1.379(6) N(13)-Cu(5)-N(14) 102.3(1) N(16)-Cu(6)-N(17) 102.4(1) N(13)-Cu(5)-N(15) 103.3(1) N(16)-Cu(6)-N(18) 103.1(1) N(14)-Cu(5)-N(15) 110.4(1) N(17)-Cu(6)-N(18) 110.8(1) N(13)-Cu(5)-C(105) 84.3(1) N(16)-Cu(6)-C(127) 81.9(1) N(14)-Cu(5)-C(105) 112.5(1) N(17)-Cu(6)-C(127) 106.0(1) N(15)-Cu(5)-C(105) 133.5(1) N(18)-Cu(6)-C(127) 140.4(1) N(13)-Cu(5)-C(106) 113.7(2) N(16)-Cu(6)-C(128) 99.9(1) N(14)-Cu(5)-C(106) 122.1(1) N(17)-Cu(6)-C(128) 130.7(1) N(15)-Cu(5)-C(106) 103.7(1) N(18)-Cu(6)-C(128) 106.0(1) C(105)-Cu(5)-C(106) 36.2(2) C(17)-Cu(6)-C(18) 35.7(1) 6
8 Table S1. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 H )]ClO 4 (1 H ) (continued). Molecule 7 Molecule 8 Cu(7)-N(19) 2.080(4) Cu(8)-N(22) 2.089(3) Cu(7)-N(21) 2.014(3) Cu(8)-N(23) 2.008(3) Cu(7)-N(20) 2.002(3) Cu(8)-N(24) 2.005(3) Cu(7)-C(149) 2.342(3) Cu(8)-C(171) 2.380(3) Cu(7)-C(150) 2.227(4) Cu(8)-C(176) 2.178(4) C(149)-C(154) 1.404(6) C(171)-C(172) 1.410(6) C(149)-C(150) 1.430(7) C(171)-C(176) 1.401(6) C(154)-C(153) 1.369(6) C(172)-C(173) 1.376(6) C(153)-C(152) 1.379(6) C(173)-C(174) 1.381(7) C(152)-C(151) 1.375(7) C(174)-C(175) 1.383(7) C(151)-C(150) 1.390(7) C(175)-C(176) 1.403(7) N(19)-Cu(7)-N(21) 103.0(1) N(22)-Cu(8)-N(23) 102.1(1) N(19)-Cu(7)-N(20) 102.8(1) N(22)-Cu(8)-N(24) 102.4(1) N(20)-Cu(7)-N(21) 111.3(1) N(23)-Cu(8)-N(24) 111.0(1) N(19)-Cu(7)-C(149) 83.9(1) N(22)-Cu(8)-C(171) 82.5(1) N(21)-Cu(7)-C(149) 133.4(1) N(23)-Cu(8)-C(171) 139.8(1) N(20)-Cu(7)-C(149) 111.7(1) N(24)-Cu(8)-C(171) 106.9(1) N(19)-Cu(7)-C(150) 113.4(2) N(22)-Cu(8)-C(176) 99.7(2) N(21)-Cu(7)-C(150) 103.1(1) N(23)-Cu(8)-C(176) 105.8(2) N(20)-Cu(7)-C(150) 121.9(2) N(24)-Cu(8)-C(176) 131.4(2) C(149)-Cu(7)-C(150) 36.6(2) C(171)-Cu(8)-C(176) 35.2(1) 7
9 Table S1. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 H )]ClO 4 (1 H ) (continued). Molecule 9 Molecule 10 Cu(9)-N(25) 2.074(3) Cu(10)-N(28) 2.097(3) Cu(9)-N(27) 2.008(4) Cu(10)-N(29) 2.005(3) Cu(9)-N(26) 2.003(4) Cu(10)-N(30) 2.015(3) Cu(9)-C(193) 2.313(4) Cu(10)-C(215) 2.322(4) Cu(9)-C(198) 2.238(5) Cu(10)-C(216) 2.188(4) C(193)-C(198) 1.379(7) C(215)-C(216) 1.402(6) C(193)-C(194) 1.409(7) C(215)-C(220) 1.404(7) C(198)-C(197) 1.443(8) C(216)-C(217) 1.391(7) C(197)-C(196) 1.367(9) C(217)-C(218) 1.392(8) C(196)-C(195) 1.353(9) C(218)-C(219) 1.395(9) C(195)-C(194) 1.377(8) C(219)-C(220) 1.357(8) N(25)-Cu(9)-N(27) 101.6(1) N(28)-Cu(10)-N(29) 102.6(1) N(25)-Cu(9)-N(26) 102.5(1) N(28)-Cu(10)-N(30) 100.7(1) N(26)-Cu(9)-N(27) 109.2(1) N(28)-Cu(10)-N(29) 102.6(1) N(25)-Cu(9)-C(193) 83.4(1) N(28)-Cu(10)-C(215) 83.6(1) N(27)-Cu(9)-C(193) 112.0(1) N(29)-Cu(10)-C(215) 107.4(1) N(26)-Cu(9)-C(193) 136.2(1) N(30)-Cu(10)-C(215) 141.6(1) N(25)-Cu(9)-C(198) 100.7(2) N(28)-Cu(10)-C(216) 100.7(1) N(27)-Cu(9)-C(198) 136.1(2) N(29)-Cu(10)-C(216) 132.6(2) N(26)-Cu(9)-C(198) 102.2(2) N(30)-Cu(10)-C(216) 106.7(2) C(193)-Cu(9)-C(198) 35.2(2) C(215)-Cu(10)-C(216) 36.1(2) 8
10 Figure S2 C26 C27 C32 C33 C15 C16 C23 C17 C22 C18 C20 C19 C21 C25 C24 C28 C31 C29 N5 Cu2 C30 C45 C44 C46 C43 C42 C40 N6 N4 C38 C34 C7 C6 C35 C36 C5 C37 C4 C3 N1 C14 N2 C2 C1 Cu1 C13 C12 N3 C8 C11 C9 C10 C39 C41 Figure S2. ORTEP diagram of [Cu I (L1 Me )]ClO 4 (1 Me ) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 9
11 Table S2. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 Me )]ClO 4 (1 Me ). Molecule 1 Molecule 2 Cu(1)-N(1) 2.104(5) Cu(2)-N(4) 2.122(5) Cu(1)-N(2) 2.046(5) Cu(2)-N(5) 2.003(5) Cu(1)-N(3) 2.029(5) Cu(2)-N(6) 1.974(4) Cu(1)-C(17) 2.336(6) Cu(2)-C(40) 2.381(6) Cu(1)-C(23) 2.147(5) Cu(2)-C(46) 2.266(5) C(17)-C(18) 1.417(8) C(40)-C(41) 1.405(8) C(17)-C(23) 1.424(7) C(40)-C(46) 1.419(9) C(18)-C(19) 1.378(9) C(41)-C(42) 1.381(8) C(19)-C(20) 1.404(8) C(42)-C(43) 1.404(9) C(20)-C(22) 1.383(7) C(43)-C(45) 1.385(8) C(22)-C(23) 1.408(8) C(45)-C(46) 1.389(9) N(1)-Cu(1)-N(2) 100.1(2) N(4)-Cu(2)-N(5) 101.8(2) N(1)-Cu(1)-N(3) 101.0(2) N(4)-Cu(2)-N(6) 101.9(2) N(2)-Cu(1)-N(3) 109.7(2) N(5)-Cu(2)-N(6) 114.3(2) N(1)-Cu(1)-C(17) 84.3(2) N(4)-Cu(2)-C(40) 82.7(2) N(2)-Cu(1)-C(17) 142.7(2) N(5)-Cu(2)-C(40) 126.1(2) N(3)-Cu(1)-C(17) 105.6(2) N(6)-Cu(2)-C(40) 117.1(2) N(1)-Cu(1)-C(23) 100.6(2) N(4)-Cu(2)-C(46) 113.3(2) N(2)-Cu(1)-C(23) 106.9(2) N(5)-Cu(2)-C(46) 100.6(2) N(3)-Cu(1)-C(23) 133.0(2) N(6)-Cu(2)-C(46) 123.3(2) C(17)-Cu(1)-C(23) 36.7(2) C(40)-Cu(2)-C(46) 35.5(2) 10
12 Figure S3 C22 C21 C20 O1 C23 C19 C16 C17 C18 C15 C7 N1 C14 C13 Cu1 N3 C12 N2 C11 C5 C2 C1 C8 C10 C9 C6 C4 C3 Figure S3. ORTEP diagram of [Cu I (L1 OMe )]ClO 4 (1 OMe ) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 11
13 Table S3. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 OMe )]ClO 4 (1 OMe ). Cu(1) N(1) 2.098(2) Cu(1) N(2) 1.981(2) Cu(1) N(3) 2.003(2) Cu(1) C(17) 2.514(2) Cu(1) C(18) 2.195(2) C(17) C(18) 1.398(3) C(17) C(22) 1.409(3) C(18) C(19) 1.408(3) C(19) C(20) 1.389(3) C(20) C(21) 1.393(3) C(21) C(22) 1.375(3) N(1) Cu(1) N(2) (7) N(1) Cu(1) N(3) (7) N(2) Cu(1) N(3) (7) N(1) Cu(1) C(17) 79.74(7) N(2) Cu(1) C(17) (7) N(3) Cu(1) C(17) (7) N(1) Cu(1) C(18) 97.37(7) N(2) Cu(1) C(18) (7) N(3) Cu(1) C(18) (8) C(17) Cu(1) C(18) 33.69(8) 12
14 Figure S4 C21 C20 Cl1 C22 C16 C17 C18 C19 C15 Cu1 N3 C8 C9 N1 C14 N2 C1 C10 C6 C7 C5 C13 C12 C11 C2 C4 C3 Figure S4. ORTEP diagram of [Cu I (L1 Cl )]ClO 4 (1 Cl ) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 13
15 Table S4. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 Cl )]ClO 4 (1 Cl ). Cu(1) N(1) 2.136(8) Cu(1) N(2) 1.968(7) Cu(1) N(3) 1.974(7) Cu(1) C(17) 2.655(9) Cu(1) C(18) 2.475(8) C(17) C(18) 1.36(1) C(17) C(22) 1.39(1) C(18) C(19) 1.36(1) C(19) C(20) 1.41(2) C(20) C(21) 1.34(2) C(21) C(22) 1.37(2) N(1) Cu(1) N(2) 104.8(3) N(1) Cu(1) N(3) 102.8(3) N(2) Cu(1) N(3) 136.5(3) N(1) Cu(1) C(18) 103.8(3) N(2) Cu(1) C(18) 107.3(3) N(3) Cu(1) C(18) 97.8(3) N(1) Cu(1) C(17) 76.8(3) N(2) Cu(1) C(17) 100.8(3) N(3) Cu(1) C(17) 117.9(3) C(17) Cu(1) C(18) 30.5(3) 14
16 Figure S5 C28 C37 C43 C44 C38 C25 C26 C27 C24 C29 N6 C23 N5 C36 C35 O7 N8 Cu2 O8 C39 C42 C40 C41 O1 N4 C21 O2 C20 C22 C19 C17 C18 C16 C15 C34 C33 N7 C32 C30 C2 C31 C1 C3 Cu1 N2 C8 C9 C5 C4 C7 N3 C6 N1 C12 C10 C13 C14 C11 Figure S5. ORTEP diagram of [Cu I (L1 NO 2 )]ClO 4 (1 NO 2 ) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 15
17 Table S5. Selected bond lengths (Å) and angles (deg) of [Cu I (L1 NO 2 )]ClO 4 (1 NO 2 ). Molecule 1 Molecule 2 Cu(1)-N(1) 2.100(4) Cu(2)-N(5) 2.130(4) Cu(1)-N(2) 1.970(4) Cu(2)-N(6) 1.980(4) Cu(1)-N(3) 1.952(5) Cu(2)-N(7) 1.966(4) Cu(1)-C(17) 2.597(5) Cu(2)-C(39) 2.595(5) Cu(1)-C(22) 2.392(5) Cu(2)-C(40) 2.383(5) C(17)-C(18) 1.398(7) C(39)-C(40) 1.407(8) C(17)-C(22) 1.399(7) C(39)-C(44) 1.404(7) C(18)-C(19) 1.357(7) C(40)-C(41) 1.404(7) C(19)-C(20) 1.387(8) C(41)-C(42) 1.403(7) C(20)-C(21) 1.374(7) C(42)-C(43) 1.379(7) C(21)-C(22) 1.412(7) C(43)-C(44) 1.391(7) N(1)-Cu(1)-N(2) 104.8(2) N(5)-Cu(2)-N(6) 102.5(2) N(1)-Cu(1)-N(3) 104.9(2) N(5)-Cu(2)-N(7) 104.1(2) N(2)-Cu(1)-N(3) 131.4(2) N(6)-Cu(2)-N(7) 133.4(2) N(1)-Cu(1)-C(17) 105.4(2) N(4)-Cu(2)-C(39) 77.7(2) N(2)-Cu(1)-C(17) 96.5(2) N(5)-Cu(2)-C(39) 101.9(2) N(3)-Cu(1)-C(17) 111.3(2) N(6)-Cu(2)-C(39) 120.8(2) N(1)Cu(1)-C(22) 105.5(2) N(5)-Cu(2)-C(40) 106.3(2) N(2)-Cu(1)-C(22) 96.5(2) N(6)-Cu(2)-C(40) 109.6(2) N(3)-Cu(1)-C(22) 111.3(2) N(7)-Cu(2)-C(40) 98.7(2) C(17)-Cu(1)-C(22) 32.2(2) C(40)-Cu(2)-C(39) 32.5(2) 16
18 Figure S6 C26 C25 C27 C28 C23 C24 C22 C21 C20 C16 C17 C18 C19 C15 N1 C13 Cu1 N3 C8 C7 C14 C5 C6 N2 C3 C2 C1 C12 C11 C10 C9 C4 Figure S6. ORTEP diagram of [Cu I (L3)]ClO 4 (3) with thermal ellipsoids at 50 % probability. The counter anions and hydrogen atoms are omitted for clarity. 17
19 Table S6. Selected bond lengths (Å) and angles (deg) of [Cu I (L3)]ClO 4 (3). Cu(1) N(1) 2.131(3) Cu(1) N(2) 2.003(4) Cu(1) N(3) 2.001(2) Cu(1) C(17) 2.347(4) Cu(1) C(18) 2.172(4) C(17) C(18) 1.419(6) C(17) C(22) 1.408(6) C(18) C(19) 1.401(6) C(19) C(20) 1.369(6) C(20) C(21) 1.395(7) C(21) C(22) 1.389(6) N(1) Cu(1) N(2) 102.1(1) N(1) Cu(1) N(3) 102.0(1) N(2) Cu(1) N(3) 115.3(1) N(1) Cu(1) C(17) 83.5(1) N(2) Cu(1) C(17) 104.3(1) N(3) Cu(1) C(17) 137.5(1) N(1) Cu(1) C(18) 98.7(1) N(2) Cu(1) C(18) 131.9(2) N(3) Cu(1) C(18) 101.8(2) C(17) Cu(1) C(18) 36.3(1) 18
20 Table S7. Selected bond lengths (Å) of the phenyl ring. [a] Complex C 1 C 2 C 2 C 3 C 3 C 4 C 4 C 5 C 5 C 6 C 6 C 1 1 H Me OMe Cl NO [b] [a] Average values are presented in case plural crystallographically independent molecules exist in the unit cell. Atomic numbers of the phenyl ring of copper(i) complexes are indicated in Figure 1. [b] Bond lengths of another phenyl ring which does not interact with the cuprous ion in 3. 19
21 Figure S7 p H p Me p OMe d / Å Cu C 1 Cu C p Cl p NO Figure S7. Optimized structures of 1 X (X = H, Me, OMe, Cl, NO 2 ) obtained by the DFT calculation with the Cu C distances. 20
22 Figure S8 4 1 NO 2 1 Cl 1 OMe 2 1 H 1 Me ln (K as ) T 1 / K 1 Figure S8. Plots of lnk as vs. T 1 for the titration of the copper(i) complexes with CH 3 CN in CH 2 Cl 2. 21
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