C11H12N2O
































 









Nitrogen


Nuclear Quadrupole Coupling Constants

in Phenazone (Antipyrine)

(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)

 








 








 

 





Calculation of the 14N nuclear quadrupole coupling constants in Phenazone was made here on an ropt molecular structure given by B3P86/6-31G(3d,3p) optimization.

These calculated nqcc's are compared with experimental values [1] in Tables 1 and 2.  Structure parameters are given in Table 3, rotational constants and electric dipole moments in Table 4.

In Tables 1 and 2, subscripts a,b,c refer to the principal axes of the inertia tensor; x,y,z to the principal axes of the nqcc tensor.  ETA = (Xxx - Xyy)/Xzz.  RMS is the root mean square difference between calculated and experimental diagonal nqcc's.  RSD is the calibration residual standard deviation of the B3PW91/6-311+G(df,pd) model for calculation of the efg's/nqcc's.

 








 








   






Table 1.  Nitrogen nqcc's in Phenazone (MHz).  Calculation was made on  B3P86/6-31G(3d,3p) ropt structure.
   









Calc
Expt [1]
   






14N(1) *
 Xaa
2.404
2.480(10)


Xbb
2.645
2.6498(98)


Xcc -
 5.049
 -
 5.1298(98)


Xab -
 1.508




Xac -
 0.301




Xbc
0.090



 







RMS
0.064 (1.9 %)




RSD
 0.030 (1.3 %)


 







Xxx
1.016




Xyy
4.046




Xzz
5.062




ETA
0.598




Ř **
15.16



 







 








* See below for atomic numbering.

** Angle (degrees) between z-principal axis and normal to C(5)N(1)N(2) plane.

 








 








   






Table 2.  Nitrogen nqcc's in Phenazone (MHz).  Calculation was made on  B3P86/6-31G(3d,3p) ropt structure.
   









Calc
Expt [1]
   






14N(2) *
 Xaa
1.849
1.780(11)


Xbb
1.146
1.100(10)


Xcc -
 2.995
 -
 2.880(10)


Xab -
 2.472




Xac -
 1.820




Xbc -
 2.576



 







RMS
0.082 (4.3 %)




RSD
 0.030 (1.3 %)


 







Xxx
1.283




Xyy
4.013




Xzz -
 5.296




ETA
0.515




Ř **
28.78



 







 








* See below for atomic numbering.

** Angle (degrees) between z-principal axis and normal to N(1)N(2)C(3) plane.

 








 








Table 3.  Phenazone.  B3P86/6-31G(3d,3p) optimized structure parameters (Ĺ and degrees).











 N
 N,1,B1
 C,2,B2,1,A1
 C,3,B3,2,A2,1,D1,0
 C,1,B4,2,A3,3,D2,0
 O,5,B5,1,A4,2,D3,0
 C,2,B6,1,A5,5,D4,0
 C,3,B7,2,A6,1,D5,0
 C,1,B8,2,A7,3,D6,0
 C,9,B9,1,A8,2,D7,0
 C,10,B10,9,A9,1,D8,0
 C,11,B11,10,A10,9,D9,0
 C,12,B12,11,A11,10,D10,0
 C,13,B13,12,A12,11,D11,0
 H,4,B14,3,A13,2,D12,0
 H,7,B15,2,A14,1,D13,0
 H,7,B16,2,A15,1,D14,0
 H,7,B17,2,A16,1,D15,0
 H,8,B18,3,A17,2,D16,0
 H,8,B19,3,A18,2,D17,0
 H,8,B20,3,A19,2,D18,0
 H,10,B21,9,A20,1,D19,0
 H,11,B22,10,A21,9,D20,0
 H,12,B23,11,A22,10,D21,0
 H,13,B24,12,A23,11,D22,0
 H,14,B25,13,A24,12,D23,0





















 B1=1.40014725
 B2=1.38702639
 B3=1.35254328
 B4=1.41579604
 B5=1.21643261
 B6=1.45897822
 B7=1.48719847
 B8=1.40759311
 B9=1.396535
 B10=1.38774059
 B11=1.39110777
 B12=1.38946602
 B13=1.38912151
 B14=1.0783293
 B15=1.09659086
 B16=1.09000281
 B17=1.08976494
 B18=1.09465351
 B19=1.09324558
 B20=1.08983059
 B21=1.08157101
 B22=1.08486751
 B23=1.08444771
 B24=1.08501135
 B25=1.08386794
  A1=106.11393749
 A2=110.69693778
 A3=110.11572607
 A4=124.44273457
 A5=113.88619866
 A6=120.07277182
 A7=119.10883341
 A8=118.97269398
 A9=119.3747218
 A10=120.83015563
 A11=119.46885354
 A12=120.46014638
 A13=127.24204108
 A14=111.72368505
 A15=109.08285403
 A16=108.61680625
 A17=111.69972708
 A18=111.32453352
 A19=109.6269765
 A20=119.3039393
 A21=119.16435551
 A22=120.28125713
 A23=120.16934907
 A24=120.74521619

  D1=-5.46664598
 D2=6.21677372
 D3=173.58410363
 D4=138.58308077
 D5=173.99875848
 D6=159.46297567
 D7=160.90997255
 D8=179.51619711
 D9=1.09635286
 D10=-0.86241691
 D11=-0.24261949
 D12=-174.88533225
 D13=-62.27318418
 D14=58.55317817
 D15=176.49384739
 D16=-71.8634135
 D17=48.69198973
 D18=168.74581672
 D19=0.68463901
 D20=-179.52672572
 D21=179.31306343
 D22=-179.23002005
 D23=-177.42126665













 













Table 3.  Phenazone.  Rotational Constants (MHz) and Electric Dipole Moments (D).







 Calc.
     Expt [1]






A
 1432.0
 1424.59526(71)

B
   500.3
   496.56384(24)

C
   400.6
   400.108793(96)






|µa|
   2.26


|µb|   5.00


|µc|   0.86




 








 








[1] P.Écija, E.J.Cocinero, A.Lesarri, J.A.Fernández, W.Caminati, and F.Castańo, J.Chem.Phys. 138,114304(2013).

 








 








Nicotine Anabasine2,3-Cyclopentenopyridine

 








 








Table of Contents




Molecules/Nitrogen




 








 













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Last Modified 3 Dec 2013