Quantum-chemical calculation of the models of dekacene and eicocene by method MNDO within the framework of molecular graphene model Текст научной статьи по специальности «Химические науки»

УДК 547.62:544.183.26

V. A. Babkin, V. V. Trifonov, A. P. Knyazev, V. Yu. Dmitriev,

D. S. Andreev, A. V. Ignatov, E. S.Titova, O. V. Stoyanov, G. E. Zaikov

QUANTUM-CHEMICAL CALCULATION OF THE MODELS OF DEKACENE AND EICOCENE

BY METHOD MNDO WITHIN THE FRAMEWORK OF MOLECULAR GRAPHENE MODEL

Keywords: quantum chemical calculation, method MNDO, dekacene, eicocene, acid strength.

Quantum-chemical calculation of molecules dekacene and eicocene was done by method MNDO. Optimized by all parameters geometric and electronic structures of these compounds was received. Each of these molecular models has a universal factor of acidity equal to 33 (pKa=33). They all pertain to class of very weak Н-acids (рКа>14).

Ключевые слова: квантово-химический расчет, метод MNDO, декацен, эйкоцен, кислотная сила.

Впервые выполнен квантово-химический расчет молекул декацена и эйкоцена методом ММБО с оптимизацией геометрии по всем параметрам стандартным градиентным методом Получено оптимизированное геометрическое и электронное строение этих соединений. Теоретически оценена их кислотная сила (рКа=33). Установлено, что эти близкие к графену соединения относятся к классу очень слабых кислот (рКа>14).

Aims and backgrounds

The aim of this work is a study of electronic structure of molecules dekacene, eicocene and theoretical estimation its acid power by quantum-chemical method MNDO within the framework of molecular graphene model, which was dicovered by Novoselov and Game in 2004 [1].

Methodical part

The calculation was done with optimization of all parameters by standard gradient method built-in in PC GAMES S [2]. The calculation was executed in approach the insulated molecule in gas phase. Program MacMolPlt was used for visual presentation of the model of the molecule. [3].

The results of the calculation and discussion

Geometric and electronic structures, general and electronic energies of moleculaes dekacene, eicocene was received by method MNDO and are shown on fig. 1, fig. 2 and in tab.1-3 . The universal factor of acidity was calculated by formula: pKa = 49,4-134,61*qmaxH+ [4] (where, qmaxH+ - a maximum positive charge on atom of the hydrogen (by Milliken [1]) R=0.97, R- a coefficient of correlations, qmaxH+=+0,06). pKa=33. This formula was successfully used in the following articles: [5, 6, 7].

Quantum-chemical calculation of molecules dekacene, eicocene by method MNDO was executed for the first time. Optimized geometric and electronic structures of these compound was received. Acid power of molecules dekacene, eicocene was theoretically evaluated (pKa=33). These compounds pertain to class of very weak H-acids (pKa>14).

Table 1 - Optimised bond lengths, valent corners and atom charges of dekacene

H52 H44 H37 H31 H26 h»9

HI 4 H8 H58 H64

H 49 H43 НЗЭ H32 H25 H20 НИ H7 Fig. 1 - Geometric and electronic molecular structure of dekacene. (Е0= -550105 kDg/mol, Eel= -4850841 kDg/mol).

Bond lengths R,A Valent comers Grad Atom Charge (by Milliken)

1 2 3 4 5 6

C(1)-C(2) 1 46 C(3)-C(2)-C(1) 118 C(1) -0.04

C(2)-C(3) 1 45 C(12)-C(9)-C(1) 122 C(2) -0.04

C(3)-C(4) 1 38 C(4)-C(3)-C(2) 123 C(3) -0.02

C(4)-C(5) 1 47 C(9)-C(1)-C(2) 119 C(4) -0.06

C(5)-C(6) 1 38 C(5)-C(4)-C(3) 119 C(5) -0.06

C(6)-C(1) 1 45 C(10)-C(2)-C(3) 123 C(6) -0.02

H(7)-C(3) 1 09 C(6)-C(5)-C(4) 119 H(7) 0.06

H(8)-C(6) 1 09 C(54)-C(53)-C(4) 123 H(8) 0.06

C(9)-C(12) 1 44 C(1)-C(6)-C(5) 123 C(9) -0.02

C(9)-C(1) 1 39 C(53)-C(4)-C(5) 118 C(10) -0.02

C(10)-C(2) 1 39 C(2)-C(1)-C(6) 118 C(11) -0.04

C(11)-C(10) 1 44 C(9)-C(1)-C(6) 123 C(12) -0.04

C(12)-C(11) 1.46 C(4)-C(3)-H(7) 120 H(13) 0.06

H(13)-C(10) 1.38 C(1)-C(6)-H(8) 117 H(14) 0.06

H(14)-C(9) 1.45 C(11)-C(12)-C(9) 118 C(15) -0.02

C(15)-C(16) 1.42 C(15)-C(12)-C(9) 123 C(16) -0.04

C(15)-C(12) 1.41 C(1)-C(2)-C(10) 119 C(17) -0.04

C(16)-C(17) 1.45 C(18)-C(11)-C(10) 123 C(18) -0.02

С(17)-C(18) 1.42 C(2)-C(10)-C(11) 122 H(19) 0.06

С(18)-C(11) 1.41 C(15)-C(12)-C(11) 119 H(20) 0.06

H(19)-C(15) 1.09 C(10)-C(11)-C(12) 118 C(21) -0.02

H(20)-C(18) 1.09 C(16)-C(15)-C(12) 122 C(22) -0.04

C(21)- C(22) 1.41 C(2)-C(10)-H(13) 120 C(23) -0.04

C(21)-C(16) 1.42 C(12)-C(9)-H(14) 118 C(24) -0.02

C(22)-C(23) 1.46 C(17)-C(16)-C(15) 119 H(25) 0.06

С(23)-C(24) 1.40 C(21)-C(16)-C(15) 123 H(26) 0.06

С(24)-C(17) 1.42 C(18)-C(17)-C(16) 119 C(27) -0.02

H(25)-C(24) 1.09 C(22)-C(21)-C(16) 122 C(28) -0.02

H(26)-C(21) 1.09 C(11)-C(18)-C(17) 122 C(29) -0.04

C(27)-C(30) 1.39 C(21)-C(16)-C(17) 119 C(30) -0.04

C(27)-C(22) 1.44 C(12)-C(11)-C(18) 119 H(31) 0.06

C(28)-c(23) 1.44 C(24)-C(17)-C(18) 123 H(32) 0.06

End table 1

1 2 3 4 5 6

C(29)-C(28) 1.39 C(16)-C(15)-H(19) 118 C(33) -0.02

C(30)-C(29) 1.46 C(11)-C(18)-H(20) 119 C(34) -0.04

H(31)-C(27) 1.09 C(23)-C(22)-C(21) 119 C(35) -0.02

H(32)-C(28) 1.09 C(27)-C(22)-C(21) 123 C(36) -0.04

C(33)-c(29) 1.45 C(24)-C(23)-C(22) 119 H(37) 0.06

C(34)- C(33) 1.38 C(30)-C(27)-C(22) 122 H(38) 0.06

C(35)-C(36) 1.38 C(17)-C(24)-C(23) 122 C(39) -0.02

C(35)-C(30) 1.45 C(27)-C(22)-C(23) 118 C(40) -0.04

C(36)-C(34) 1.47 C(16)-C(17)-C(24) 119 C(41) -0.04

H(37)-C(35) 1.09 C(28)-C(23)-C(24) 123 C(42) -0.02

H(38)-C(33) 1.09 C(17)-C(24)-H(25) 119 H(43) 0.06

C(39)-C(40) 1.38 C(22)-C(21)-H(26) 119 H(44) 0.06

C(39)-C(36) 1.46 C(29)-C(30)-C(27) 119 C(45) -0.04

C(40)-C(41) 1.48 C(35)-C(30)-C(27) 123 C(46) -0.06

C(41)- C(42) 1.38 C(22)-C(23)-C(28) 118 C(47) -0.06

C(42)-C(34) 1.46 C(33)-C(29)-C(28) 123 C(48) -0.04

H(43)-C(42) 1.09 C(23)-C(28)-C(29) 122 H(49) 0.06

H(44)-C(39) 1.09 C(35)-C(30)-C(29) 118 H(50) 0.06

C(45)- C(46) 1.36 C(28)-C(29)-C(30) 119 H(51) 0.06

C(45)- C(40) 1.47 C(36)-C(35)-C(30) 124 H(52) 0.06

C(46)-C(47) 1.45 C(30)-C(27)-H(31) 120 C(53) -0.02

C(47)-C(48) 1.36 C(23)-C(28)-H(32) 118 C(54) -0.04

C(48)-C(41) 1.47 C(30)-C(29)-C(33) 118 C(55) -0.04

H(49)-C(48) 1.09 C(42)-C(34)-C(33) 123 C(56) -0.02

H(50)-C(47) 1.09 C(29)-C(33)-C(34) 123 H(57) 0.06

H(51)-C(46) 1.09 C(39)-C(36)-C(34) 118 H(58) 0.06

H(52)-C(45) 1.09 C(34)-C(36)-C(35) 119 C(59) -0.04

C(53)-C(54) 1.38 C(39)-C(36)-C(35) 123 C(60) -0.06

C(53)-C(4) 1.46 C(33)-C(34)-C(36) 119 C(61) -0.06

C(54)- C(55) 1.48 C(40)-C(39)-C(36) 123 C(62) -0.04

C(55)-C(56) 1.38 C(36)-C(35)-H(37) 120 H(63) 0.06

C(56)-C(5) 1.46 C(29)-C(33)-H(38) 117 H(64) 0.06

H(57)-C(53) 1.09 C(41)-C(40)-C(39) 119 H(65) 0.06

H(58)-C(56) 1.09 C(45)-C(40)-C(39) 123 H(66) 0.06

C(59)- C(60) 1.36 C(42)-C(41)-C(40) 119

C(59)-C(54) 1.47 C(46)-C(45)-C(40) 122

C(60)-C(61) 1.45 C(34)-C(42)-C(41) 123

C(61)- C(62) 1.36 C(45)-C(40)-C(41) 118

C(62)-C(55) 1.47 C(36)-C(34)-C(42) 118

H(63)-C(59) 1.09 C(48)-C(41)-C(42) 123

H(64)-C(62) 1.09 C(34)-C(42)-H(43) 117

H(65)-C(61) 1.09 C(40)-C(39)-H(44) 120

H(66)-C(60) 1.09 C(47)-C(46)-C(45) 121

C(48)-C(47)-C(46) 121

C(41)-C(48)-C(47) 122

C(40)-C(41)-C(48) 118

C(41)-C(48)-H(49) 118

C(48)-C(47)-H(50) 121

C(47)-C(46)-H(51) 118

C(46)-C(45)-H(52) 120

C(55)-C(54)-C(53) 119

C(3)-C(4)-C(53) 123

C(56)-C(55)-C(54) 119

C(60)-C(59)-C(54) 122

C(5)-C(56)-C(55) 123

C(59)-C(54)-C(55) 118

C(4)-C(5)-C(56) 118

C(6)-C(5)-C(56) 123

C(54)-C(53)-H(57) 120

C(5)-C(56)-H(58) 117

C(61)-C(60)-C(59) 121

C(53)-C(54)-C(59) 123

C(62)-C(61)-C(60) 121

C(55)-C(62)-C(61) 122

C(54)-C(55)-C(62) 118

C(56)-C(55)-C(62) 123

C(60)-C(59)-H(63) 120

C(55)-C(62)-H(64) 118

C(62)-C(61)-H(65) 121

C(61)-C(60)-H(66) 118

Fig. 2 - Geometric and electronic molecular structure of eicocene. (E0= -1069853 kDg/mol, Ee,= -11719827 kDg/mol)

Table 2 - Optimised bond lengths, valent corners and atom charges of eicocene

Bond lengths R,A Valence corners Grad Atom Charge (by Milliken)

1 2 3 4 5 6

C(2)-C(1) 1.46 C(5)-C(6)-C(1) 122 C(1) -0.03

C(3)-C(2) 1.44 C(11)-C(10)-C(2) 122 C(2) -0.04

C(4)-C(3) 1.39 C(1)-C(2)-C(3) 118 C(3) -0.02

C(4)-C(5) 1.47 C(10)-C(2)-C(3) 123 C(4) -0.04

C(5)-C(54) 1.46 C(5)-C(4)-C(3) 119 C(5) -0.04

C(6)-C(5) 1.39 C(2)-C(3)-C(4) 122 C(6) -0.02

C(6)-C(1) 1.44 C(54)-C(5)-C(4) 118 H(7) +0.06

H(7)-C(3) 1.09 C(6)-C(5)-C(4) 119 H(8) +0.06

H(8)-C(6) 1.09 C(53)-C(54)-C(5) 123 C(9) -0.02

C(9)-C(1) 1.40 C(54)-C(5)-C(6) 123 C(10) -0.02

C(10)-C(2) 1.40 C(2)-C(1)-C(6) 118 C(11) -0.03

C(10)-C(11) 1.43 C(2)-C(3)-H(7) 118 C(12) -0.03

C(11)-C(18) 1.42 C(5)-C(6)-H(8) 120 H(13) +0.06

C(11)-C(12) 1.45 C(1)-C(6)-H(8) 118 H(14) +0.06

C(12)-C(9) 1.43 C(2)-C(1)-C(9) 119 C(15) -0.02

H(13)-C(10) 1.09 C(1)-C(2)-C(10) 119 C(16) -0.04

H(14)-C(9) 1.09 C(18)-C(11)-C(10) 123 C(17) -0.04

C(15)-C(12) 1.42 C(12)-C(11)-C(10) 119 C(18) -0.02

C(16)-C(15) 1.41 C(17)-C(18)-C(11) 122 H(19) +0.06

C(16)-C(17) 1.45 C(9)-C(12)-C(11) 119 H(20) +0.06

C(17)-C(24) 1.44 C(15)-C(12)-C(11) 119 C(21) -0.02

C(18)-C(17) 1.41 C(1)-C(9)-C(12) 122 C(22) -0.04

H(19)-C(15) 1.09 C(18)-C(11)-C(12) 119 C(23) -0.04

H(20)-C(18) 1.09 C(2)-C(10)-H(13) 119 C(24) -0.02

C(21)-C(16) 1.44 C(11)-C(10)-H(13) 118 H(25) +0.06

C(22)-C(21) 1.39 C(1)-C(9)-H(14) 119 H(26) +0.06

C(23)-C(22) 1.46 C(9)-C(12)-C(15) 123 C(27) -0.02

C(24)-C(23) 1.39 C(17)-C(16)-C(15) 119 C(28) -0.02

H(25)-C(24) 1.09 C(12)-C(15)-C(16) 122 C(29) -0.04

H(26)-C(21) 1.09 C(24)-C(17)-C(16) 118 C(30) -0.04

Continuation table 2

1 2 3 4 5 6

C(27)-C(22) 1.45 C(18)-C(17)-C(16) 119 H(31) +0.06

C(28)-C(23) 1.45 C(23)-C(24)-C(17) 122 H(32) +0.06

C(29)-C(28) 1.38 C(24)-C(17)-C(18) 123 C(33) -0.02

C(29)-C(30) 1.47 C(12)-C(15)-H(19) 119 C(34) -0.04

C(30)-C(27) 1.38 C(17)-C(18)-H(20) 119 C(35) -0.02

H(31)-C(27) 1.09 C(15)-C(16)-C(21) 123 C(36) -0.04

H(32)-C(28) 1.09 C(17)-C(16)-C(21) 118 H(37) +0.06

C(33)-C(29) 1.46 C(16)-C(21)-C(22) 122 H(38) +0.06

C(34)-C(33) 1.38 C(21)-C(22)-C(23) 119 C(39) -0.02

C(34)-C(36) 1.48 C(27)-C(22)-C(23) 118 C(40) -0.04

C(34)-C(42) 1.46 C(22)-C(23)-C(24) 119 C(41) -0.04

C(35)-C(30) 1.46 C(28)-C(23)-C(24) 123 C(42) -0.02

C(36)-C(35) 1.38 C(23)-C(24)-H(25) 120 H(43) +0.06

H(37)-C(35) 1.09 C(16)-C(21 )-H(26) 118 H(44) +0.06

H(38)-C(33) 1.09 C(21)-C(22)-C(27) 123 C(45) -0.02

C(39)-C(36) 1.46 C(22)-C(23)-C(28) 118 C(46) -0.03

C(40)-C(39) 1.38 C(30)-C(29)-C(28) 119 C(47) -0.03

C(40)-C(41) 1.48 C(23)-C(28)-C(29) 123 C(48) -0.02

C(41)-C(48) 1.45 C(27)-C(30)-C(29) 119 H(49) +0.05

C(42)-C(41) 1.38 C(35)-C(30)-C(29) 118 H(50) +0.05

H(43)-C(42) 1.09 C(22)-C(27)-C(30) 123 C(51) -0.02

H(44)-C(39) 1.09 C(22)-C(27)-H(31) 117 C(52) -0.04

C(45)-C(40) 1.45 C(23)-C(28)-H(32) 117 C(53) -0.04

C(46)-C(45) 1.39 C(28)-C(29)-C(33) 123 C(54) -0.02

C(47)-C(46) 1.49 C(30)-C(29)-C(33) 118 H(55) +0.06

C(48)-C(47) 1.39 C(36)-C(34)-C(33) 120 H(56) +0.06

H(49)-C(48) 1.09 C(42)-C(34)-C(33) 123 C(57) -0.04

H(50)-C(45) 1.09 C(29)-C(33)-C(34) 123 C(58) -0.06

C(51)-C(4) 1.46 C(35)-C(36)-C(34) 120 C(59) -0.06

C(52)-C(51) 1.38 C(41)-C(42)-C(34) 123 C(60) -0.04

C(52)-C(53) 1.48 C(39)-C(36)-C(34) 118 H(61) +0.06

C(53)-C(60) 1.47 C(27)-C(30)-C(35) 123 H(62) +0.06

C(54)-C(53) 1.38 C(30)-C(35)-C(36) 123 H(63) +0.06

H(55)-C(51) 1.09 C(42)-C(34)-C(36) 118 H(64) +0.06

H(56)-C(54) 1.09 C(30)-C(35)-H(37) 117 C(65) -0.04

C(57)-C(52) 1.47 C(29)-C(33)-H(38) 117 C(66) -0.04

C(58)-C(57) 1.36 C(35)-C(36)-C(39) 123 C(67) -0.02

C(59)-C(58) 1.45 C(41)-C(40)-C(39) 119 C(68) -0.04

C(60)-C(59) 1.36 C(36)-C(39)-C(40) 123 C(69) -0.04

H(61)-C(57) 1.09 C(48)-C(41)-C(40) 118 C(70) -0.02

H(62)-C(60) 1.09 C(42)-C(41)-C(40) 119 H(71) +0.06

H(63)-C(59) 1.09 C(47)-C(48)-C(41) 124 H(72) +0.06

H(64)-C(58) 1.09 C(48)-C(41)-C(42) 123 C(73) -0.02

C(65)-C(70) 1.46 C(41)-C(42)-H(43) 120 C(74) -0.02

C(66)-C(65) 1.47 C(36)-C(39)-H(44) 117 C(75) -0.04

C(67)-C(66) 1.46 C(39)-C(40)-C(45) 123 C(76) -0.04

C(68)-C(67) 1.37 C(41)-C(40)-C(45) 118 H(77) +0.06

C(68)-C(69) 1.48 C(40)-C(45)-C(46) 124 H(78) +0.06

C(69)-C(120) 1.46 C(45)-C(46)-C(47) 119 C(79) -0.02

C(70)-C(69) 1.38 C(124)-C(46)-C(47) 118 C(80) -0.04

H(71)-C(67) 1.09 C(46)-C(47)-C(48) 119 C(81) -0.04

H(72)-C(70) 1.09 C(123)-C(47)-C(48) 123 C(82) -0.02

C(73)-C(65) 1.38 C(47)-C(48)-H(49) 119 H(83) +0.06

C(74)-C(66) 1.38 C(40)-C(45)-H(50) 117 H(84) +0.06

C(75)-C(74) 1.46 C(3)-C(4)-C(51) 123 C(85) -0.02

C(75)-C(76) 1.47 C(5)-C(4)-C(51) 118 C(86) -0.03

C(76)-C(73) 1.46 C(53)-C(52)-C(51) 119 C(87) -0.04

H(77)-C(74) 1.09 C(4)-C(51)-C(52) 123 C(88) -0.02

H(78)-C(73) 1.09 C(60)-C(53)-C(52) 118 H(89) +0.06

C(79)-C(76) 1.39 C(54)-C(53)-C(52) 119 H(90) +0.06

C(80)-C(79) 1.45 C(59)-C(60)-C(53) 122 C(91) -0.02

C(80)-C(81) 1.46 C(60)-C(53)-C(54) 123 C(92) -0.02

C(81)-C(82) 1.45 C(4)-C(51)-H(55) 117 C(93) -0.04

C(82)-C(75) 1.39 C(53)-C(54)-H(56) 120 C(94) -0.04

H(83)-C(79) 1.09 C(51)-C(52)-C(57) 123 H(95) +0.06

H(84)-C(82) 1.09 C(53)-C(52)-C(57) 118 H(96) +0.06

C(85)-C(80) 1.40 C(52)-C(57)-C(58) 122 C(97) -0.02

C(86)-C(85) 1.43 C(57)-C(58)-C(59) 121 C(98) -0.04

C(86)-C(87) 1.45 C(58)-C(59)-C(60) 121 C(99) -0.02

C(87)-C(88) 1.43 C(52)-C(57)-H(61) 118 C(100) -0.04

C(88)-C(81) 1.40 C(59)-C(60)-H(62) 120 H(101) +0.06

H(89)-C(88) 1.09 C(58)-C(59)-H(63) 118 H(102) +0.06

H(90)-C(85) 1.09 C(57)-C(58)-H(64) 121 C(103) -0.02

C(91)-C(86) 1.42 C(69)-C(70)-C(65) 123 C(104) -0.04

C(92)-C(87) 1.42 C(70)-C(65)-C(66) 118 C(105) -0.04

C(93)-C(92) 1.41 C(73)-C(65)-C(66) 119 C(106) -0.02

C(93)-C(94) 1.45 C(65)-C(66)-C(67) 118 H(107) +0.06

C(94)-C(91) 1.41 C(74)-C(66)-C(67) 123 H(108) +0.06

H(95)-C(91) 1.09 C(69)-C(68)-C(67) 120 C(109) -0.04

H(96)-C(92) 1.09 C(66)-C(67)-C(68) 123 C(110) -0.06

C(97)-C(93) 1.44 C(120)-C(69)-C(68) 118 C(111) -0.06

C(98)-C(97) 1.39 C(70)-C(69)-C(68) 120 C(112) -0.04

C(98)-C(100) 1.46 C(119)-C(120)- 123 H(113) +0.06

C(69)

C(98)-C(106) 1.45 C(120)-C(69)-C(70) 123 H(114) +0.06

C(99)-C(94) 1.44 C(66)-C(67)-H(71) 117 H(115) +0.06

C(100)-C(99) 1.39 C(69)-C(70)-H(72) 120 H(116) +0.06

H(101)-C(99) 1.09 C(70)-C(65)-C(73) 123 C(117) -0.02

H(102)-C(97) 1.09 C(65)-C(66)-C(74) 119 C(118) -0.04

C(103)- C(100) 1.45 C(76)-C(75)-C(74) 118 C(119) -0.04

C(104)-C(103) 1.38 C(66)-C(74)-C(75) 123 C(120) -0.02

C(104)-C(105) 1.47 C(73)-C(76)-C(75) 118 H(121) +0.05

C(105)- C(112) 1.47 C(79)-C(76)-C(75) 119 H(122) +0.05

C(106)-C(105) 1.38 C(65)-C(73)-C(76) 123 C(123) -0.02

H(107)-C(106) 1.09 C(66)-C(74)-H(77) 120 C(124) -0.02

H(108)-C(103) 1.09 C(65)-C(73)-H(78) 120 H(125) +0.05

C(109)-C(104) 1.47 C(73)-C(76)-C(79) 123 H(126) +0.05

C(110)-C(109) 1.36 C(81)-C(80)-C(79) 118

C(111)-C(110) 1.45 C(76)-C(79)-C(80) 122

C(112)-C(111) 1.36 C(82)-C(81)-C(80) 118

H(113)-C(112) 1.09 C(88)-C(81)-C(80) 119

H(114)-C(111) 1.09 C(75)-C(82)-C(81) 122

H(115)-C(110) 1.09 C(74)-C(75)-C(82) 123

H(116)-C(109) 1.09 C(76)-C(75)-C(82) 119

C(117)-C(68) 1.46 C(76)-C(79)-H(83) 120

C(118)-C(117) 1.38 C(75)-C(82)-H(84) 120

C(118)-C(119) 1.49 C(79)-C(80)-C(85) 123

C(118)-C(123) 1.44 C(81)-C(80)-C(85) 119

C(119)-c(124) 1.44 C(87)-C(86)-C(85) 119

C(120)-C(119) 1.38 C(80)-C(85)-C(86) 122

H(121)-C(117) 1.09 C(88)-C(87)-C(86) 119

H(122)-C(120) 1.09 C(92)-C(87)-C(86) 119

C(123)-C(47) 1.42 C(81)-C(88)-C(87) 122

C(124)-C(46) 1.42 C(82)-C(81)-C(88) 123

H(125)-C(123) 1.09 C(81 )-C(8 8)-H(89) 119

H(126)-C(124) 1.09 C(80)-C(85)-H(90) 119

C(85)-C(86)-C(91) 123

C(87)-C(86)-C(91) 119

C(88)-C(87)-C(92) 123

C(94)-C(93)-C(92) 119

C(87)-C(92)-C(93) 122

C(91)-C(94)-C(93) 119

C(99)-C(94)-C(93) 118

C(86)-C(91)-C(94) 122

C(86)-C(91 )-H(95) 119

C(87)-C(92)-H(96) 119

C(92)-C(93)-C(97) 123

C(94)-C(93)-C(97) 118

C(100)-C(98)-C(97) 119

C(106)-C(98)-C(97) 123

C(93)-C(97)-C(98) 122

C(99)-C(100)-C(98) 119

C(105)-C(106)-C(98) 123

C(103)-C(100)-C(98) 118

C(91)-C(94)-C(99) 123

C(94)-C(99)-C(100) 122

C(106)-C(98)-C(100) 118

C(94)-C(99)-H(101) 118

C(93)-C(97)-H(102) 118

C(99)-C(100)-C(103) 123

C(105)-C(104)-C(103) 119

End table 2

1 2 3 4 5 6

C(100)-C(103)-C(104) 123

C(112)-C(105)-C(104) 118

C(106)-C(105)-C(104) 119

C(111)-C(112)-C(105) 122

C(112)-C(105)-C(106) 123

C(105)-C(106)-H(107) 120

C(100)-C(103)-H(108) 117

C(103)-C(104)-C(109) 123

C(105)-C(104)-C(109) 118

C(104)-C(109)-C(110) 122

C(109)-C(110)-C(111) 121

C(110)-C(111)-C(112) 121

C(111)-C(112)-H(113) 120

C(110)-C(111)-H(114) 118

C(109)-C(110)-H(115) 121

C(104)-C(109)-H(116) 118

C(67)-C(68)-C(117) 123

C(69)-C(68)-C(117) 118

C(119)-C(118)-C(117) 119

C(123)-C(118)-C(117) 123

C(68)-C(117)-C(118) 123

C(124)-C(119)-C(118) 118

C(47)-C(123)-C(118) 124

C(120)-C(119)-C(118) 119

C(46)-C(124)-C(119) 124

C(123)-C(118)-C(119) 118

C(124)-C(119)-C(120) 123

C(68)-C(117)-H(121) 117

C(119)-C(120)-H(122) 120

C(46)-C(47)-C(123) 118

C(45)-C(46)-C(124) 123

C(47)-C(123)-H(125) 118

C(46)-C(124)-H(126) 118

Table 3 - Total energy (E0), maximal charge on the hydrogen atom (qmaxH+ ) and universal factor of acidity (pKa) of molecules dekacene and eicocene

Molecules Eq (kDg/mol) a H+ Hmax pKa

Dekacene -550105 +0.06 33

Eicocene -1069853 +0.06 33

References

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