Antioxidant Properties of Lapachol and Its Derivatives and Their Ability to Chelate Iron (II) Cation: DFT and QTAIM Studies

Table 2

Values of ligand...Fe²⁺ distance, NBO charge carried by Fe²⁺ cation, and topological parameters of ligand...Fe²⁺ interactions at B3LYP/6-311++G(d,p) (bold face numbers related to X…Fe²⁺ interaction and lower italicized numbers related to Y⋯Fe²⁺ interaction).

Complexes

Ligand...Fe^2+separation distance (Å)

Q/e

Eint

(au)

(au)

(kJ/mol)

(kJ/mol)

(kJ/mol)

ɛ

k^2-O1,O2

aLa2

1.908; 1.981

1.432; 1.422

−1876.9; –

0.0880; 0.0690

0.618; 0.486

−6.120; 5.970

411.805; 313.125

−417.924; −307.151

−0.0447; 0.6175

0.7587; −0.0458

−0.0959; −0.0855

1.146224; 0.866129

aLa3

1.843; 1.921

1.008

−976.6

0.1090; 0.0860

0.720; 0.564

−36.700; −10.430

509.125; 380.935

−545.829; −391.364

0.9478; −0.0670

−0.0820; 0.7692

−0.1460; −0.1377

0.780231; 1.054578

aLa4

1.835; 1.922

1.027; 1.234

−956.6

0.1110; 0.0850

0.736; 0.561

−41.019; −9.506

524.223; 377.715

−565.243; −387.221

−0.0802; 0.7740

0.9712; −0.0712

−0.1548; −0.1418

0.930247; 0.991469

aLa5

1.844; 1.937

0.990; –

−961.8; –

0.1070; 0.8010

0.724; 0.544

−33.340; −3.618

508.850; 360.761

−542.190; −364.380

−0.0731; 0.7237

0.9355; 0.0724

−0.1380; −0.1175

0.887768; 0.890006

aLa6

1.835; 1.922

0.990; 1.421

−2558.1; –

0.1110; 0.0840

0.729; 0.573

−39.050; −6.510

517.854; 382.941

−556.905; −389.454

0.9616; −0.0658

−0.0791; 0.7581

−0.1529; −0.1188

0.932448; 0.804333

aLa7

1.851; 1.947

0.963; –

−2594.9; –

0.1050; 0.7700

0.715; 0.536

−28.530; −0.129

497.552; 351.920

−526.082; −352.048

−0.0686; 0.6933

0.9111; −0.5591

−0.1280; −0.1015

0.866595; 0.815607

k^2 −O2,O

aLa52

1.786; 1.884

0.767; 1.046

−1151.2; −

0.2870; 0.3300

−0.801; −0.945

−864.007; −921.327

337.436; 300.811

−1200.786; −1222.138

0.3667; 0.3617

−0.5037; −0.7243

−0.6643; −0.5828

0.318769; 0.242798

k^2 −O3,O

aLa53

1.808; 1.871

0.839; 1.130

−1178.7; −

0.1190; 0.0980

0.802; 0.662

−53.830; −19.278

580.507; 454.053

−634.338; −473.331

1.0499; −0.1565

−0.096; −0.5406

−0.1518; 0.8729

0.585220; 1.893919

k^3 −(O2,C=C)

bLa1

1.784; 2.004; 2.038

0.618; 0.997; –

−20183.7; –; –

0.1320; 0.1070; 0.0960

0.764; 0.245; 0.2576

−86.608; −93.192; −73.442

588.395; 253.906; 242.528

−675.003; −347.099; −315.969

1.1899; −0.1017; −0.1015

−0.2043; 0.4728; 0.4260

−0.2212; −0.1263; −0.0669

0.082728; 0.241748; 0.516271

bLa2

2.053; 1.980

0.674; 1.002; 0.820

−941.0; –; –

0.0527; 0.1139; –

0.429; 0.3026; –

−17.738; −10.454; –

263.930; 303.147; –

−246.192; −407.689; –

0.4645; −0.1129; –

−0.0233; 0.5230; –

−0.0121; −0.1075; –

0.919931; 0.049950; –

bLa3

1.772; 2.039; 1.981

0.538; –; –

−1105.1; –; –

0.1389; 0.1022; 0.1179

0.7834; 0.2961; 0.2555

−100.780; −80.968; −115.288

614.954; 275.341; 282.988

−715.734; −356.309; −398.276

1.2696; −0.0569; −0.1461

−0.2022; 0.4603; 0.5267

−0.2840; −0.1072; −0.1251

0.404762; 0.883927; 0.168423

bLa6

1.918; 1.919; 2.325

0.607; –; –

−2612.5; –

0.0885; 0.1343

0.5752; 0.2583

−11.925; −148.704

389.493; 318.259

−401.418; −466.963

0.7561; −0.1922

−0.1154; 0.6103

−0.6549; −0.1598

0.762316; 0.202276

bLa7

1.808; 2.119; 2.025

0.521; 0.843; –

−105952.8; −; −

0.1264; 0.8184; 0.1015

0.6941; 0.2114; 0.1803

−77.219; −52.574; −87.858

532.792; 191.359; 206.175

−610.011; −243.933; −294.033

1.1400; −0.6246; −0.1288

−0.1991; 0.3506; 0.4422

−0.2468; −0.0767; −0.1331

0.239906; 0.228563; 0.032791

k^2 −(O3,C=C)

cLa1

1.799; 2.003; 2.040

0.618; 0.967; –

−1152.30; –; –

0.1240; 0.1078; 0.0965

0.7783; 0.2088; 0.2382

−69.056; −95.037; −74.481

579.899; 232.059; 230.842

−648.955; −327.097; −305.323

1.1161; −0.1074; −0.1079

−0.2081; 0.4731; 0.4266

−0.1297; −0.1570; −0.0805

0.603944; 0.462709; 0.341246

cLa2

1.788; 2.156; 2.119

1.016; 1.046; 0.848

−1101.3; –; –

0.1303; 0.0759; 0.0840

0.8045; 0.1458; 0.1610

−81.455; −48.375; −61.404

609.483; 144.063; 167.050

−690.936; −192.437; −228.454

0.1162; −0.0663; −0.1038

−0.1942; 0.3069; 0.3440

−0.1638; −0.9477; −0.0792

0.185365; 0.428508; 0.311229

cLa3

1.794; 2.037; 1.984

0.513; –; –

−1118.3; –; –

0.1267; 0.1012; 0.1175

0.782; 0.286; 0.245

−74.266; −79.636; −114.417

587.632; 267.377; 275.450

−661.899; −347.013; −389.866

1.1585; −0.0544; −0.1450

−0.1937; 0.4481; 0.5182

−0.1827; −0.1076; −0.1269

0.060095; 0.976210; 0.150727

cLa6

1.865; 2.080; 2.098

0.948; –; –

−1198.5; –; –

0.1046; 0.0910; 0.0858

0.6198; 0.2369; 0.2252

−35.057; −65.729; −58.587

441.884; 221.198; 206.406

−476.941; −286.927; −264.993

0.9067; −0.0935; −0.1007

−0.1091; 0.3927; 0.3712

−0.1778; −0.6229; −0.0453

0.630515; 0.501621; 1.223375

cLa7

1.821; 2.083; 2.014

0.521; 0.521; 1.062

−105980.9; –; –

0.1171; 0.0491; 0.0887

0.6875; 0.1972; 0.2172

−57.602; −17.174; −62.854

508.853; 146.584; 205.422

−566.455; −163.758; −268.275

1.0486; −0.0464; −0.7478

−0.2032; −0.0677; 0.3783

−0.1579; 0.3113; −0.8634

0.287284; 0.458724; 0.154464