Structure, Stability and Interaction Studies on Schiff Base Analogue Systems
Abstract
:Introduction
Computational details
Results and Discussion
NMP-Water Interaction: Geometries and Energetics
Parameters | MP2 | B3LYP | B3PW91 | MP2 | B3LYP | B3PW91 | MM | AM1 |
---|---|---|---|---|---|---|---|---|
NMP | NMP-Water along CH side | |||||||
R(C1-N2) | 1.471 | 1.470 | 1.462 | 1.470 | 1.468 | 1.461 | 1.491 | 1.446 |
R(N2-C3) | 1.299 | 1.300 | 1.298 | 1.299 | 1.302 | 1.299 | 1.285 | 1.314 |
R(C3-C4) | 1.435 | 1.433 | 1.431 | 1.436 | 1.434 | 1.432 | 1.447 | 1.446 |
R(C4-C5) | 1.349 | 1.349 | 1.348 | 1.350 | 1.349 | 1.347 | 1.345 | 1.345 |
R(N2-H9) | 1.023 | 1.020 | 1.019 | 1.022 | 1.020 | 1.019 | 1.023 | 1.009 |
R(H10-O14) | … | … | … | 2.015 | 2.040 | 1.987 | … | … |
R(O14-H15) | … | … | … | 0.972 | 0.970 | 0.968 | … | … |
θ(Χ1−Ν2−Χ3) | 125.8 | 126.2 | 126.2 | 124.7 | 125.5 | 125.4 | … | … |
θ(Ν2−Χ3−Χ4) | 123.8 | 124.2 | 124.1 | 123.7 | 123.8 | 123.8 | 122.6 | 124.1 |
θ(Χ3−Χ4−Χ5) | 119.3 | 120.0 | 119.9 | 118.0 | 118.9 | 118.7 | 121.0 | 121.2 |
θ(Ν2−Χ1−Η7) | 108.8 | 109.1 | 109.1 | 109.0 | 109.3 | 109.4 | 111.0 | 111.1… |
θ(Χ3−Η10−Ο14) | … | … | … | 167.5 | 158.9 | 167.5 | … | … |
θ(Η15−Ο14−Η16) | … | … | … | 104.4 | 104.5 | 104.7 | … | … |
θ(Χ1−Ν2−Χ3−Χ4) | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 | … | … |
θ(Ν2−Χ3−Χ4−Χ5) | 180.0 | 180.0 | 180.0 | 180.0 | 179.0 | 180.0 | … | … |
-E | 210.9906 | 211.72692 | 211.64397 | 287.21062 | 288.15841 | 288.0467 | … | … |
Eint | … | … | … | 14.680 | 14.310 | 13.420 | … | … |
μΜ | 0.2484 | 0.6997 | 0.7234 | 0.385 | 1.096 | 0.907 | … | … |
RA | 27.5885 | 27.8687 | 27.9141 | 2.8978 | 3.164 | 2.9314 | … | … |
RB | 2.2447 | 2.2331 | 2.2443 | 2.1488 | 2.0104 | 2.1483 | … | … |
RC | 2.1036 | 1.095 | 2.105 | 1.251 | 1.2462 | 1.2569 | … | … |
η | 6.18* | … | … | 6.23* | … | … | … | … |
μ | -9.27* | … | … | -8.75* | … | … | … | … |
NMP-Water along NH side | NMP-2Water | |||||||
R(C1-N2) | 1.466 | 1.465 | 1.457 | 1.465 | 1.464 | 1.457 | ||
R(N2-C3) | 1.296 | 1.297 | 1.294 | 1.297 | 1.299 | 1.296 | ||
R(C3-C4) | 1.439 | 1.438 | 1.435 | 1.440 | 1.439 | 1.437 | ||
R(C4-C5) | 1.348 | 1.347 | 1.346 | 1.349 | 1.347 | 1.346 | ||
R(N2-H9) | 1.041 | 1.043 | 1.043 | 1.038 | 1.038 | 1.039 | ||
R(H9-O14) | 1.772 | 1.761 | 1.741 | 1.795 | 1.785 | 1.7673 | ||
R(O14-H15) | 0.972 | 0.971 | 0.968 | 0.972 | 0.970 | 0.9679 | ||
R(H10-O17) | … | … | … | 2.069 | 2.077 | 2.031 | ||
R(O17-H18) | … | … | … | 0.971 | 0.970 | 0.968 | ||
θ(Χ1−Ν2−Χ3) | 124.9 | 125.2 | 125.1 | 124.0 | 124.7 | 124.5 | ||
θ(Ν2−Χ3−Χ4) | 123.0 | 123.7 | 123.6 | 122.8 | 123.2 | 123.2 | ||
θ(Χ3−Χ4−Χ5) | 119.4 | 120.0 | 119.9 | 118.3 | 119.1 | 118.8 | ||
θ(Ν2−Χ1−Η7) | 108.8 | 109.2 | 109.2 | 109.0 | 109.4 | 109.4 | ||
θ(Ν2−Η9−Ο14) | 171.2 | 169.9 | 172.4 | 171.4 | 170.0 | 172.2 | ||
θ(Η15−Ο14−Η16) | 105.2 | 105.4 | 105.5 | 105.1 | 105.3 | 105.5 | ||
θ(Χ3−Η10−Ο17) | … | … | … | 164.0 | 158.8 | 166.7 | ||
θ(Η18−Ο17−Η19) | … | … | … | 104.3 | 104.4 | 104.6 | ||
θ(Χ1−Ν2−Χ3−Χ4) | 180.0 | 180.0 | 180.0 | 180.0 | 179.9 | 180.0 | ||
θ(Ν2−Χ3−Χ4−Χ5) | 180.0 | 180.0 | 180.0 | 180.1 | 179.9 | 180.0 | ||
-E | 287.2197 | 288.16697 | -288.05537 | 363.43722 | 364.59589 | 364.45557 | ||
Eint | 20.53 | 19.91 | 19.13 | 34.06 | 32.93 | 31.30 | ||
μΜ | 0.5266 | 1.2245 | 1.2897 | 0.62 | 1.3803 | 1.3676 | ||
RA | 3.2714 | 3.2906 | 3.3688 | 2.4032 | 2.4413 | 2.3936 | ||
RB | 2.0295 | 2.0317 | 1.9999 | 1.1159 | 1.1151 | 1.1307 | ||
RC | 1.2701 | 1.2739 | 1.2726 | 0.7713 | 0.7748 | 0.7773 | ||
η | 6.21* | … | … | 6.25* | … | … | ||
μ | -8.68* | … | … | -8.20* | … | … |
Parameters | MP2 | B3LYP | B3PW91 | MP2 | B3LYP | B3PW91 |
---|---|---|---|---|---|---|
NMB | NMB-Water along CH side | |||||
R(C1-N2) | 1.470 | 1.468 | 1.460 | 1.470 | 1.468 | 1.460 |
1.302 | 1.305 | 1.303 | 1.302 | 1.305 | 1.303 | |
R(C3-C4) | 1.427 | 1.424 | 1.421 | 1.429 | 1.426 | 1.424 |
R(C4-C5) | 1.359 | 1.362 | 1.361 | 1.357 | 1.360 | 1.359 |
R(C5-C6) | 1.489 | 1.487 | 1.482 | 1.790 | 1.489 | 1.483 |
R(N2-H10) | 1.023 | 1.020 | 1.019 | 1.022 | 1.019 | 1.018 |
R(C3-H11) | 1.087 | 1.087 | 1.087 | 1.090 | 1.091 | 1.092 |
R(H11-O17) | … | … | … | 2.074 | 2.056 | 2.057 |
θ(Χ1−Ν2−Χ3) | 125.8 | 126.2 | 126.2 | 124.8 | 125.3 | 125.4 |
θ(Ν2−Χ3−Χ4) | 123.1 | 123.8 | 123.7 | 122.6 | 123.1 | 123.0 |
θ(Χ3−Χ4−Χ5) | 122.8 | 123.4 | 123.3 | 122.2 | 122.9 | 122.9 |
θ Χ4−Χ5−Χ6 | 129.0 | 129.4 | 129.5 | 128.5 | 129.1 | 129.1 |
θ(Χ3−Η11−Ο17) | … | … | … | 165.0 | 165.0 | 165.1 |
θ(Η18−Ο17−Η19 | … | … | … | 104.3 | 104.5 | 104.6 |
θ(Χ1−Ν2−Χ3−Χ4) | 180.1 | 180.2 | 180.1 | 180.0 | 180.0 | 180.0 |
θ(Ν2−Χ3−Χ4−Χ5) | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 |
θ(Χ3−Χ4−Χ5−Χ6) | 0.1 | 0.1 | 0.1 | 0.0 | 0.0 | 0.0 |
-E | 250.16614 | 251.05361 | 250.9573 | 326.3872 | 327.48529 | 327.36 |
Eint | … | … | … | 15.3 | 14.45 | 13.4 |
μΜ | 1.5137 | 1.8032 | 1.7934 | 1.0178 | 1.3734 | 1.3692 |
RA | 10.8426 | 10.9277 | 10.9743 | 2.5135 | 2.5375 | 2.5355 |
RB | 1.5148 | 1.5011 | 1.5081 | 1.4902 | 1.475 | 1.4805 |
RC | 1.3516 | 1.3419 | 1.3482 | 0.9508 | 0.9479 | 0.9499 |
η | 5.98* | … | … | 6.31* | … | … |
μ | -8.80* | … | … | -8.35* | … | … |
NMB-Water along NH side | NMB-2Water | |||||
R(C1-N2) | 1.465 | 1.464 | 1.456 | 1.466 | 1.465 | 1.457 |
R(N2-C3) | 1.300 | 1.301 | 1.299 | 1.300 | 1.302 | 1.300 |
R(C3-C4) | 1.432 | 1.429 | 1.426 | 1.434 | 1.431 | 1.429 |
R(C4-C5) | 1.357 | 1.358 | 1.357 | 1.356 | 1.357 | 1.356 |
R(C5-C6) | 1.491 | 1.489 | 1.484 | 1.492 | 1.491 | 1.486 |
R(N2-H10) | 1.040 | 1.039 | 1.040 | 1.031 | 1.036 | 1.037 |
R(C3-H11 | 1.088 | 1.088 | 1.088 | 1.089 | 1.090 | 1.092 |
R(H10-O17) | 1.784 | 1.776 | 1.759 | 1.806 | 1.798 | 1.782 |
R(H11-O20) | … | … | … | 2.104 | 2.090 | 2.093 |
θ(Χ1−Ν2−Χ3) | 124.8 | 125.2 | 125.2 | 124 | 124.4 | 124.4 |
θ(Ν2−Χ3−Χ4) | 122.4 | 123.2 | 123.2 | 121.9 | 122.7 | 122.5 |
θ(Χ3−Χ4−Χ5) | 122.9 | 123.4 | 123.3 | 122.3 | 122.9 | 122.9 |
θ(Χ4−Χ5−Χ6) | 129 | 129.4 | 129.5 | 128.5 | 129.1 | 129.1 |
θ(Ν2−Η10−Ο17) | 172.1 | 170.9 | 173.1 | 172.7 | 171.4 | 173.7 |
θ(Η18−Ο17−Η19) | 105.2 | 105.4 | 105.5 | 105.1 | 105.3 | 105.5 |
θ(Χ3−Η11−Ο20) | … | … | … | 165.4 | 165.5 | 165.6 |
θ(Η21−Ο20−Η22) | … | … | … | 104.3 | 104.5 | 104.6 |
θ(Χ1−Ν2−Χ3−Χ4) | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 |
θ(Ν2−Χ3−Χ4−Χ5) | 180.1 | 180.0 | 180.0 | 180.0 | 180.0 | 180.0 |
θ(Χ3−Χ4−Χ5−Χ6) | 0 | 0 | 0 | 0 | 0 | 0 |
-E | 326.39380 | 327.49182 | 327.36690 | 402.6126 | 403.92125 | 403.76735 |
Eint | 19.61 | 18.76 | 18.00 | 33.90 | 32.07 | 30.29 |
μΜ | 1.8595 | 2.3063 | 2.3093 | 1.3112 | 1.878 | 1.8962 |
RA | 3.0968 | 3.1039 | 3.1727 | 1.5716 | 1.5693 | 1.581 |
RB | 1.1816 | 1.1787 | 1.1679 | 1.0083 | 1.0119 | 1.0052 |
RC | 0.8681 | 0.8670 | 0.8663 | 0.6226 | 0.6236 | 0.6229 |
η | 6.01* | … | … | 6.05* | … | … |
μ | -8.26* | … | … | -7.83* | … | … |
NMB-water Interaction: Geometries and Energetics
Atom | NMP | NMP-Water along CH | Atom | NMP-Water along NH | NMP-2 Water | ||||
---|---|---|---|---|---|---|---|---|---|
NPA | MPA | NPA | MPA | NPA | MPA | NPA | MPA | ||
C1 | -0.418 | -0.325 | -0.417 | -0.322 | C1 | -0.420 | -0.322 | -0.419 | -319 |
N2 | -0.569 | -0.663 | -0.578 | -0.674 | N2 | -0.577 | -0.708 | -0.586 | -0.719 |
C3 | 0.340 | 0.258 | 0.331 | 0.210 | C3 | 0.3324 | 0.237 | 0.317 | 0.194 |
C4 | -0.412 | -0.257 | -0.410 | -0.265 | C4 | -0.398 | -0.259 | -0.397 | -0.270 |
C5 | -0.161 | -0.295 | -0.173 | -0.309 | C5 | -0.194 | -0.310 | -0.203 | -0.325 |
H6 | 0.240 | 0.228 | 0.242 | 0.231 | H6 | 0.235 | 0.219 | 0.237 | 0.221 |
H7 | 0.256 | 0.250 | 0.250 | 0.240 | H7 | 0.250 | 0.238 | 0.244 | 0.230 |
H8 | 0.256 | 0.250 | 0.250 | 0.240 | H8 | 0.250 | 0.238 | 0.244 | 0.230 |
H9 | 0.461 | 0.453 | 0.455 | 0.446 | H9 | 0.498 | 0.541 | 0.492 | 0.535 |
H10 | 0.250 | 0.300 | 0.282 | 0.380 | H10 | 0.254 | 0.286 | 0.273 | 0.363 |
H11 | 0.267 | 268 | 0.260 | 0.259 | H11 | 0.274 | 0.279 | 0.267 | 0.270 |
H12 | 0.233 | 0.254 | 0.242 | 0.264 | H12 | 0.229 | 0.244 | 0.239 | 0.258 |
H13 | 0.2579 | 0.279 | 0.250 | 0.267 | H13 | 0.252 | 0.266 | 0.244 | 0.254 |
O14 | … | … | -1.010 | -0.906 | O14 | -1.013 | -0.912 | -1.01 | -0.909 |
H15 | … | … | 0.514 | 0.469 | H15 | 0.524 | 0.481 | 0.521 | 0.477 |
H16 | … | … | 0.514 | 0.470 | H16 | 0.524 | 0.481 | 0.521 | 0.477 |
O17 | … | … | -1.005 | -0.90 | |||||
H18 | … | … | 0.510 | 0.466 | |||||
H19 | … | … | 0.510 | 0.466 |
Atom | NMB | NMB-Water along CH | Atom | NMB-Water along NH | NMB-2 Water | ||||
---|---|---|---|---|---|---|---|---|---|
NPA | MPA | NPA | MPA | NPA | MPA | NPA | MPA | ||
C1 | -0.417 | -0.32 | -0.422 | -0.335 | C1 | -0.419 | -0.318 | -0.424 | -0.333 |
N2 | -0.578 | -0.672 | -0.581 | -0.681 | N2 | -0.585 | -0.717 | -0.587 | -0.727 |
C3 | 0.342 | 0.262 | 0.333 | 0.219 | C3 | 0.328 | 0.242 | 0.320 | 0.200 |
C4 | -0.442 | -0.315 | -0.437 | -0.319 | C4 | -0.429 | -0.321 | -0.424 | -0.323 |
C5 | 0.059 | -0.053 | 0.046 | -0.060 | C5 | 0.028 | -0.067 | 0.016 | -0.073 |
C6 | -0.710 | -0.562 | -0.713 | -0.574 | C6 | -0.705 | -0.556 | -0.708 | -0.569 |
H7 | 0.253 | 0.246 | 0.245 | 0.233 | H7 | 0.248 | 0.234 | 0.239 | 0.222 |
H8 | 0.237 | 0.224 | 254 | 0.249 | H8 | 0.232 | 0.215 | 0.249 | 0.241 |
H9 | 0.253 | 0.246 | 0.245 | 0.233 | H9 | 0.247 | 0.235 | 0.239 | 0.222 |
H10 | 0.458 | 0.449 | 0.451 | 0.441 | H10 | 0.495 | 0.539 | 0.488 | 0.533 |
H11 | 0.244 | 0.292 | 0.274 | 0.372 | H11 | 0.236 | 0.279 | 0.265 | 0.360 |
H12 | 0.263 | 0.257 | 0.258 | 0.249 | H12 | 0.272 | 0.271 | 0.267 | 0.274 |
H13 | 0.259 | 0.270 | 0.254 | 0.262 | H13 | 0.253 | 0.259 | 0.248 | 0.251 |
H14 | 0.227 | 0.191 | 0.239 | 0.209 | H14 | 0.224 | 0.187 | 0.237 | 0.206 |
H15 | 0.276 | 0.243 | 0.268 | 0.231 | H15 | 0.270 | 0.235 | 0.262 | 0.223 |
H16 | 0.276 | 0.243 | 0.268 | 0.231 | H16 | 0.270 | 0.235 | 0.262 | 0.223 |
017 | … | … | -0.008 | -0.900 | 017 | -1.011 | -0.910 | -1.001 | -0.907 |
H18 | … | … | 0.514 | 0.469 | H18 | 0.523 | 0.479 | 0.520 | 0.476 |
H19 | … | … | 0.514 | 0.469 | H19 | 0.523 | 0.479 | 0.520 | 0.476 |
O20 | … | … | -1.004 | -0.896 | |||||
H21 | … | … | 0.512 | 0.466 | |||||
H22 | … | … | 0.512 | 0.466 |
Parameters | NMP | Parameters | NMB | ||
---|---|---|---|---|---|
ρ | ▽2ρ | ρ | ▽2ρ | ||
Water along | Water along | ||||
NH side | NH side | ||||
O(14)-H(9) | 0.030 | 0.103 | O(17)-H(10) | 0.029 | 0.101 |
O(14)-H(11) | 0.005 | 0.021 | O(17)-H(12) | 0.004 | 0.187 |
Water along CH side | Water along CH side | ||||
O(14)-H(10) | 0.019 | 0.065 | O(17)-H(11) | 0.016 | 0.058 |
O(14)-H(12) | 0.005 | 0.021 | O(17)-H(8) | 0.007 | 0.027 |
O(17)-H(14) | 0.005 | 0.022 | |||
Water at both | |||||
sides | Water at both | ||||
O(14)-H(9) | 0.028 | 0.097 | sides | ||
O(14)-H(11) | 0.004 | 0.020 | O(17)-H(10) | 0.027 | 0.095 |
O(17)-H(10) | 0.018 | 0.062 | O(17)-H(12) | 0.004 | 0.020 |
O(17)-H(12) | 0.004 | 0.019 | O(20)-H(8) | 0.006 | 0.026 |
O(20)-H(11) | 0.015 | 0.055 | |||
O(20)-H(14) | 0.005 | 0.021 |
Conclusion
Acknowledgement
References
- Rothschild, K. J.; Argade, P. V.; Earnest, T. N.; Huang, K.-S.; London, E.; Liao, M.-J.; Bayley, H.; Khorana, H. G.; Herzfeld, J. J. Biol. Chem. 1982, 257, 8592.
- Nina, M.; Roux, B.; Smith, J. C. Biophys. J. 1995, 68, 25.
- De Groot, H.J.M.; Smith, S.O.; Courtin, J.; van der Berg, E.; Winkel, C.; Lugtenburg, J.; Griffin, R.G.; Herzfeld. J. Biochem. 1990, 29, 6873.
- Gat, Y.; Sheves, M. J. Am. Chem. Soc. 1993, 115, 3772. [CrossRef]
- Nina, M.; Smith, J.C.; Roux, B. J. Mol. Struct. (Theochem). 1993, 286, 231. [CrossRef]
- Møller, C.; Plesset, M.S. Phys. Rev. 1934, 46, 618. [CrossRef]
- Becke, A.D. Phys. Rev. A. 1988, 38, 3098. [CrossRef]
- Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B. 1988, 37, 785. [CrossRef]
- Perdew, J.P.; Wang, Y. Phys. Rev. B. 1992, 45, 244. [CrossRef]
- Boys, S. F; Bernardi, F. Mol Phys. 1970, 19, 553. [CrossRef]
- Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery Jr., J.A.; Stratmann, R.E.; Burant, J.C.; S. Dapprich, J. M.; Millam, A. D.; Daniels, K. N.; Kudin, M. C.; Strain, Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J.J.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Baboul, A.G.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.L.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Andres, J.L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian98, Revision A.11.2; Gaussian, Inc.: Pittsburgh PA, 2001. [Google Scholar]
- Deng, H.; Huang, L.; Groesbeek, M.; Lugtenburg, L.; Callender, R.H. J. Phys. Chem. 1994, 98, 4776. [CrossRef]
- Pearson, R.G. J. Chem. Edu. 1987, 64, 561. [CrossRef]
- Tajkhorshid, E.; Suhai, S. J. Phys. Chem. B 1999, 103, 5581.
- Arulmozhiraja, S.; Kolandaivel, P. Int. J. Quant. Chem. 1996, 64, 221.
- Kanakaraju, R.; Kolandaivel, P.; Gowenlock, B.G. J. Mol. Struct. (Theochem). 2002, 577, 121. [CrossRef]
- Bader, R.F.W. Atoms in Molecules. A quantum Theory; Oxford University Press: Oxford, 1990. [Google Scholar]
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Kolandaivel, P.; Kanakaraju, R. Structure, Stability and Interaction Studies on Schiff Base Analogue Systems. Int. J. Mol. Sci. 2004, 5, 1-12. https://doi.org/10.3390/i5010001
Kolandaivel P, Kanakaraju R. Structure, Stability and Interaction Studies on Schiff Base Analogue Systems. International Journal of Molecular Sciences. 2004; 5(1):1-12. https://doi.org/10.3390/i5010001
Chicago/Turabian StyleKolandaivel, P., and R. Kanakaraju. 2004. "Structure, Stability and Interaction Studies on Schiff Base Analogue Systems" International Journal of Molecular Sciences 5, no. 1: 1-12. https://doi.org/10.3390/i5010001