Literature DB >> 21578381

1-(2-Methyl-5-nitro-phenyl)guanidinium picrate.

Jerry P Jasinski, Ray J Butcher, M T Swamy, H S Yathirajan, A R Ramesha.   

Abstract

In the crystal strupan> class="Chemical">cture of the title salt, C(8)H(11)N(4)O(2) (+)·C(6)H(2)N(3)O(7) (-), the pictrate anion participates in extensive hydrogen bonding with the guanidinium ion group of the cation, linking the mol-ecules through N(+)-H⋯O(-) hydrogen bonds and inter-molecular N-H⋯O and C-H⋯O inter-actions. These hydrogen-bonding configurations involve two three-centre/bifurcated bonds [N-H⋯(O,O)] that are observed between two N atoms from the guanidinium ion group of the cation and the o-NO(2) and phenolate O atoms of the picrate anion. In addition, π-π inter-actions also contribute to the crystal packing, with a centroid-to-centroid distance of 3.693 (6) Å and a slippage angle of 1.614°. A significant number of conformational differences are observed between the salt in the crystal structure and the models obtained by density functional theory (DFT) calculations of the geometry-optimized structure.

Entities:  

Year:  2009        PMID： 21578381      PMCID： PMC2971333          DOI： 10.1107/S1600536809037647

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background literature, see: Berlinpan> class="Chemical">ck (2002 ▶); Heys et al. (2000 ▶); Ishikawa & Isobe (2002 ▶); Kelley et al. (2001 ▶); Laeckmann et al. (2002 ▶); Moroni et al. (2001 ▶); Orner & Hamilton (2001 ▶); Zyss et al. (1993 ▶). For related structures, see: Cunningham et al. (1997 ▶); Demir et al. (2006 ▶); Gupta & Dutta (1975 ▶); Moghimi et al. (2005 ▶); Murtaza et al. (2007 ▶, 2009 ▶); Pereira Silva et al. (2007 ▶); Pruszynski et al. (1992 ▶); Ren et al. (2007 ▶); Sonar et al. (2007 ▶); Smith et al. (2007 ▶, 2007a ▶); Stanford et al. (2007 ▶); Stępień & Grabowski (1977 ▶); Wang et al. (2009 ▶); Wei (2008 ▶). For density functional theory (DFT), see: Becke (1988 ▶, 1993 ▶); Frisch et al. (2004 ▶); Hehre et al. (1986 ▶); Lee et al. (1988 ▶); Schmidt & Polik (2007 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶); Bruno et al. (2004 ▶).

Experimental

Crystal data

n class="Chemical">C8pan> class="Species">H11N4O2 +·C6H2N3O7 − M = 423.31 Trin class="Chemical">clinin class="Chemical">c, a = 7.1318 (10) Å b = 10.6239 (13) Å n class="Chemical">c = 11.9564 (13) Å α = 84.257 (10)° β = 74.497 (11)° γ = 77.559 (11)° V = 851.58 (18) Å3 Z = 2 n class="Chemical">Cu Kα radiation μ = 1.23 mm−1 T = 110 K 0.51 × 0.41 × 0.33 mm

Data collection

Oxford Xn class="Chemical">calibur diffrapan> class="Chemical">ctometer with Ruby (Gemini Cu) detector Absorption n class="Chemical">correpan> class="Chemical">ction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.431, T max = 1.000 6248 measun class="Disease">red reflepan> class="Chemical">ctions 3344 independent reflen class="Chemical">ctions 2761 reflen class="Chemical">ctions with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.118 S = 1.07 3344 reflen class="Chemical">ctions 272 parameters H-atom parameters n class="Chemical">constrained Δρmax = 0.27 e Å−3 Δρmin = −0.29 e Å−3 Data n class="Chemical">collepan> class="Chemical">ction: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. n class="Chemical">Crystal strupan> class="Chemical">cture: contains datablocks global, I. DOI: 10.1107/S1600536809037647/kp2228sup1.cif Strun class="Chemical">cture fapan> class="Chemical">ctors: contains datablocks I. DOI: 10.1107/S1600536809037647/kp2228Isup2.hkl Additional supplementary materials: n class="Chemical">crystallographipan> class="Chemical">c information; 3D view; checkCIF report
C8H11N4O2+·C6H2N3O7−Z = 2
Mr = 423.31F(000) = 436
Triclinic, P1Dx = 1.651 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.1318 (10) ÅCell parameters from 3632 reflections
b = 10.6239 (13) Åθ = 4.3–73.8°
c = 11.9564 (13) ŵ = 1.23 mm−1
α = 84.257 (10)°T = 110 K
β = 74.497 (11)°Chunk, pale yellow
γ = 77.559 (11)°0.51 × 0.41 × 0.33 mm
V = 851.58 (18) Å3
Oxford Xcalibur diffractometer with Ruby (Gemini Cu) detector3344 independent reflections
Radiation source: Enhance (Cu) X-ray Source2761 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 10.5081 pixels mm-1θmax = 73.9°, θmin = 4.3°
ω scansh = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −13→13
Tmin = 0.431, Tmax = 1.000l = −14→12
6248 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0696P)2 + 0.2349P] where P = (Fo2 + 2Fc2)/3
3344 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O1A0.6186 (2)0.42327 (13)1.18314 (12)0.0358 (3)
O2A0.5417 (2)0.62511 (13)1.13392 (12)0.0383 (3)
N1A0.6304 (2)0.51540 (14)1.11228 (13)0.0261 (3)
N2A0.9515 (2)0.68299 (13)0.73199 (12)0.0228 (3)
H2AA1.04520.72220.73760.027*
N3A0.7069 (2)0.67430 (13)0.64072 (12)0.0236 (3)
H3AB0.64160.70480.58770.028*
H3AC0.67620.60760.68650.028*
N4A0.8981 (2)0.82883 (13)0.58308 (12)0.0225 (3)
H4AA0.83360.86000.52990.027*
H4AB0.99430.86440.59090.027*
C1A1.0118 (2)0.44934 (16)0.77518 (15)0.0229 (3)
C2A0.9141 (2)0.57363 (15)0.80935 (14)0.0208 (3)
C3A0.7870 (2)0.59582 (16)0.91843 (14)0.0221 (3)
H3AA0.72040.68070.94000.026*
C4A0.7597 (2)0.49070 (16)0.99526 (14)0.0225 (3)
C5A0.8533 (2)0.36602 (16)0.96653 (15)0.0246 (4)
H5AA0.83270.29561.02080.029*
C6A0.9788 (3)0.34633 (16)0.85597 (15)0.0254 (4)
H6AA1.04370.26100.83470.030*
C7A1.1495 (3)0.42731 (18)0.65702 (16)0.0298 (4)
H7AA1.08240.47060.59790.045*
H7AB1.18800.33450.64450.045*
H7AC1.26820.46240.65130.045*
C8A0.8505 (2)0.72837 (15)0.65149 (14)0.0202 (3)
O1B0.59719 (17)0.85654 (11)0.47353 (10)0.0254 (3)
O21B0.84884 (19)1.00632 (12)0.36978 (12)0.0319 (3)
O22B0.7546 (2)1.15265 (12)0.24729 (12)0.0324 (3)
O41B0.3034 (2)1.09649 (12)0.03718 (11)0.0318 (3)
O42B0.1500 (3)0.93647 (15)0.08197 (15)0.0518 (5)
O61B0.2382 (2)0.64362 (13)0.39470 (12)0.0351 (3)
O62B0.3584 (2)0.69013 (14)0.52904 (12)0.0353 (3)
N2B0.7376 (2)1.05245 (13)0.30647 (12)0.0236 (3)
N4B0.2629 (2)1.00057 (14)0.09892 (13)0.0292 (3)
N6B0.3236 (2)0.71124 (14)0.43296 (12)0.0243 (3)
C1B0.5286 (2)0.88544 (15)0.38719 (14)0.0206 (3)
C2B0.5836 (2)0.98569 (15)0.29955 (14)0.0211 (3)
C3B0.4980 (2)1.02404 (16)0.20829 (14)0.0224 (3)
H3BA0.53641.09240.15550.027*
C4B0.3543 (3)0.96112 (16)0.19447 (14)0.0237 (3)
C5B0.3011 (2)0.85874 (16)0.26861 (14)0.0230 (3)
H5BA0.20800.81370.25540.028*
C6B0.3831 (2)0.82270 (15)0.36097 (14)0.0217 (3)
U11U22U33U12U13U23
O1A0.0411 (8)0.0400 (8)0.0270 (7)−0.0189 (6)−0.0048 (6)0.0092 (6)
O2A0.0393 (8)0.0368 (8)0.0319 (7)−0.0027 (6)−0.0007 (6)−0.0020 (6)
N1A0.0239 (7)0.0325 (8)0.0248 (7)−0.0119 (6)−0.0070 (6)0.0014 (6)
N2A0.0240 (7)0.0239 (7)0.0247 (7)−0.0118 (6)−0.0099 (6)0.0048 (6)
N3A0.0255 (7)0.0248 (7)0.0243 (7)−0.0104 (6)−0.0114 (6)0.0063 (5)
N4A0.0227 (7)0.0246 (7)0.0239 (7)−0.0101 (5)−0.0096 (6)0.0042 (5)
C1A0.0220 (8)0.0269 (8)0.0236 (8)−0.0084 (6)−0.0096 (6)−0.0005 (6)
C2A0.0211 (8)0.0240 (8)0.0216 (8)−0.0101 (6)−0.0099 (6)0.0036 (6)
C3A0.0206 (8)0.0227 (8)0.0262 (8)−0.0064 (6)−0.0103 (7)0.0003 (6)
C4A0.0214 (8)0.0284 (9)0.0211 (8)−0.0105 (6)−0.0076 (6)0.0013 (6)
C5A0.0277 (9)0.0238 (8)0.0275 (9)−0.0126 (7)−0.0121 (7)0.0048 (6)
C6A0.0286 (9)0.0212 (8)0.0298 (9)−0.0073 (7)−0.0115 (7)−0.0011 (7)
C7A0.0312 (9)0.0307 (9)0.0271 (9)−0.0075 (7)−0.0054 (7)−0.0024 (7)
C8A0.0195 (8)0.0207 (8)0.0193 (7)−0.0032 (6)−0.0031 (6)−0.0018 (6)
O1B0.0296 (6)0.0253 (6)0.0264 (6)−0.0099 (5)−0.0138 (5)0.0039 (5)
O21B0.0288 (7)0.0328 (7)0.0420 (7)−0.0141 (5)−0.0201 (6)0.0092 (6)
O22B0.0406 (7)0.0278 (7)0.0374 (7)−0.0190 (6)−0.0184 (6)0.0089 (5)
O41B0.0458 (8)0.0249 (6)0.0293 (7)−0.0084 (5)−0.0183 (6)0.0044 (5)
O42B0.0762 (11)0.0455 (9)0.0594 (10)−0.0350 (8)−0.0505 (9)0.0193 (8)
O61B0.0454 (8)0.0334 (7)0.0345 (7)−0.0234 (6)−0.0129 (6)0.0028 (5)
O62B0.0369 (7)0.0442 (8)0.0326 (7)−0.0218 (6)−0.0176 (6)0.0158 (6)
N2B0.0251 (7)0.0224 (7)0.0253 (7)−0.0087 (6)−0.0072 (6)0.0005 (5)
N4B0.0382 (8)0.0246 (8)0.0308 (8)−0.0088 (6)−0.0179 (7)0.0015 (6)
N6B0.0218 (7)0.0248 (7)0.0266 (7)−0.0076 (6)−0.0054 (6)0.0020 (6)
C1B0.0201 (8)0.0194 (7)0.0227 (8)−0.0032 (6)−0.0060 (6)−0.0024 (6)
C2B0.0209 (8)0.0203 (8)0.0237 (8)−0.0061 (6)−0.0062 (6)−0.0024 (6)
C3B0.0253 (8)0.0197 (8)0.0223 (8)−0.0052 (6)−0.0056 (6)−0.0015 (6)
C4B0.0281 (9)0.0242 (8)0.0224 (8)−0.0060 (7)−0.0116 (7)−0.0020 (6)
C5B0.0227 (8)0.0227 (8)0.0259 (8)−0.0066 (6)−0.0075 (7)−0.0034 (6)
C6B0.0209 (8)0.0213 (8)0.0233 (8)−0.0057 (6)−0.0055 (6)0.0001 (6)
O1A—N1A1.2306 (19)C7A—H7AA0.9800
O2A—N1A1.217 (2)C7A—H7AB0.9800
N1A—C4A1.468 (2)C7A—H7AC0.9800
N2A—C8A1.344 (2)O1B—C1B1.241 (2)
N2A—C2A1.4363 (19)O21B—N2B1.2334 (18)
N2A—H2AA0.8800O22B—N2B1.2278 (18)
N3A—C8A1.317 (2)O41B—N4B1.2364 (19)
N3A—H3AB0.8800O42B—N4B1.227 (2)
N3A—H3AC0.8800O61B—N6B1.2250 (19)
N4A—C8A1.325 (2)O62B—N6B1.2280 (19)
N4A—H4AA0.8800N2B—C2B1.4534 (19)
N4A—H4AB0.8800N4B—C4B1.445 (2)
C1A—C2A1.398 (2)N6B—C6B1.463 (2)
C1A—C6A1.401 (2)C1B—C2B1.457 (2)
C1A—C7A1.497 (2)C1B—C6B1.460 (2)
C2A—C3A1.384 (2)C2B—C3B1.374 (2)
C3A—C4A1.386 (2)C3B—C4B1.390 (2)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.381 (2)C4B—C5B1.385 (2)
C5A—C6A1.391 (2)C5B—C6B1.368 (2)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—H6AA0.9500
O2A—N1A—O1A123.73 (15)C1A—C7A—H7AC109.5
O2A—N1A—C4A118.54 (14)H7AA—C7A—H7AC109.5
O1A—N1A—C4A117.73 (15)H7AB—C7A—H7AC109.5
C8A—N2A—C2A123.28 (13)N3A—C8A—N4A120.59 (14)
C8A—N2A—H2AA118.4N3A—C8A—N2A120.75 (14)
C2A—N2A—H2AA118.4N4A—C8A—N2A118.67 (14)
C8A—N3A—H3AB120.0O22B—N2B—O21B122.00 (13)
C8A—N3A—H3AC120.0O22B—N2B—C2B118.56 (13)
H3AB—N3A—H3AC120.0O21B—N2B—C2B119.43 (13)
C8A—N4A—H4AA120.0O42B—N4B—O41B122.85 (15)
C8A—N4A—H4AB120.0O42B—N4B—C4B118.43 (14)
H4AA—N4A—H4AB120.0O41B—N4B—C4B118.72 (14)
C2A—C1A—C6A117.73 (16)O61B—N6B—O62B122.78 (14)
C2A—C1A—C7A121.12 (15)O61B—N6B—C6B117.97 (14)
C6A—C1A—C7A121.14 (16)O62B—N6B—C6B119.25 (13)
C3A—C2A—C1A121.89 (14)O1B—C1B—C2B124.20 (14)
C3A—C2A—N2A118.23 (15)O1B—C1B—C6B124.04 (15)
C1A—C2A—N2A119.82 (15)C2B—C1B—C6B111.76 (14)
C2A—C3A—C4A118.15 (15)C3B—C2B—N2B116.04 (14)
C2A—C3A—H3AA120.9C3B—C2B—C1B124.33 (14)
C4A—C3A—H3AA120.9N2B—C2B—C1B119.63 (14)
C5A—C4A—C3A122.45 (16)C2B—C3B—C4B118.92 (15)
C5A—C4A—N1A119.67 (14)C2B—C3B—H3BA120.5
C3A—C4A—N1A117.86 (15)C4B—C3B—H3BA120.5
C4A—C5A—C6A118.22 (15)C5B—C4B—C3B121.16 (15)
C4A—C5A—H5AA120.9C5B—C4B—N4B119.33 (14)
C6A—C5A—H5AA120.9C3B—C4B—N4B119.48 (14)
C5A—C6A—C1A121.56 (16)C6B—C5B—C4B119.76 (15)
C5A—C6A—H6AA119.2C6B—C5B—H5BA120.1
C1A—C6A—H6AA119.2C4B—C5B—H5BA120.1
C1A—C7A—H7AA109.5C5B—C6B—C1B123.85 (15)
C1A—C7A—H7AB109.5C5B—C6B—N6B116.32 (14)
H7AA—C7A—H7AB109.5C1B—C6B—N6B119.79 (14)
C6A—C1A—C2A—C3A−0.7 (2)O1B—C1B—C2B—C3B−175.27 (16)
C7A—C1A—C2A—C3A−179.70 (15)C6B—C1B—C2B—C3B4.9 (2)
C6A—C1A—C2A—N2A176.60 (13)O1B—C1B—C2B—N2B4.3 (3)
C7A—C1A—C2A—N2A−2.4 (2)C6B—C1B—C2B—N2B−175.56 (14)
C8A—N2A—C2A—C3A−94.78 (19)N2B—C2B—C3B—C4B177.91 (15)
C8A—N2A—C2A—C1A87.8 (2)C1B—C2B—C3B—C4B−2.5 (3)
C1A—C2A—C3A—C4A0.8 (2)C2B—C3B—C4B—C5B−2.0 (3)
N2A—C2A—C3A—C4A−176.51 (13)C2B—C3B—C4B—N4B179.95 (15)
C2A—C3A—C4A—C5A−0.3 (2)O42B—N4B—C4B—C5B−4.7 (3)
C2A—C3A—C4A—N1A177.78 (13)O41B—N4B—C4B—C5B176.06 (16)
O2A—N1A—C4A—C5A−176.41 (15)O42B—N4B—C4B—C3B173.45 (18)
O1A—N1A—C4A—C5A3.7 (2)O41B—N4B—C4B—C3B−5.8 (3)
O2A—N1A—C4A—C3A5.4 (2)C3B—C4B—C5B—C6B3.5 (3)
O1A—N1A—C4A—C3A−174.45 (14)N4B—C4B—C5B—C6B−178.40 (15)
C3A—C4A—C5A—C6A−0.3 (2)C4B—C5B—C6B—C1B−0.7 (3)
N1A—C4A—C5A—C6A−178.34 (14)C4B—C5B—C6B—N6B−178.21 (15)
C4A—C5A—C6A—C1A0.4 (2)O1B—C1B—C6B—C5B176.90 (16)
C2A—C1A—C6A—C5A0.1 (2)C2B—C1B—C6B—C5B−3.2 (2)
C7A—C1A—C6A—C5A179.07 (15)O1B—C1B—C6B—N6B−5.6 (2)
C2A—N2A—C8A—N3A1.0 (2)C2B—C1B—C6B—N6B174.21 (14)
C2A—N2A—C8A—N4A−179.04 (15)O61B—N6B—C6B—C5B13.8 (2)
O22B—N2B—C2B—C3B14.1 (2)O62B—N6B—C6B—C5B−165.22 (16)
O21B—N2B—C2B—C3B−164.83 (15)O61B—N6B—C6B—C1B−163.84 (16)
O22B—N2B—C2B—C1B−165.51 (15)O62B—N6B—C6B—C1B17.1 (2)
O21B—N2B—C2B—C1B15.6 (2)
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O22Bi0.882.203.0737 (18)171
N3A—H3AB···O1B0.882.032.7866 (18)143
N3A—H3AB···O62B0.882.353.0882 (18)142
N3A—H3AC···O1Aii0.882.322.9808 (19)132
N4A—H4AA···O1B0.881.982.7499 (18)145
N4A—H4AA···O21B0.882.343.0683 (19)141
N4A—H4AB···O21Bi0.882.112.9572 (18)163
C3A—H3AA···O41Biii0.952.373.262 (2)155
C7A—H7AB···O1Biv0.982.563.447 (2)151
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2A—H2AA⋯O22Bi0.882.203.0737 (18)171
N3A—H3AB⋯O1B0.882.032.7866 (18)143
N3A—H3AB⋯O62B0.882.353.0882 (18)142
N3A—H3AC⋯O1Aii0.882.322.9808 (19)132
N4A—H4AA⋯O1B0.881.982.7499 (18)145
N4A—H4AA⋯O21B0.882.343.0683 (19)141
N4A—H4AB⋯O21Bi0.882.112.9572 (18)163
C3A—H3AA⋯O41Biii0.952.373.262 (2)155
C7A—H7AB⋯O1Biv0.982.563.447 (2)151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  13 in total

1.  Modified guanidines as chiral auxiliaries.

Authors:  Tsutomu Ishikawa; Toshio Isobe
Journal:  Chemistry       Date:  2002-02-02       Impact factor: 5.236

2.  First synthesis of totally orthogonal protected alpha-(trifluoromethyl)- and alpha-(difluoromethyl)arginines.

Authors:  M Moroni; B Koksch; S N Osipov; M Crucianelli; M Frigerio; P Bravo; K Burger
Journal:  J Org Chem       Date:  2001-01-12       Impact factor: 4.354

3.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

4.  Retrieval of crystallographically-derived molecular geometry information.

Authors:  Ian J Bruno; Jason C Cole; Magnus Kessler; Jie Luo; W D Sam Motherwell; Lucy H Purkis; Barry R Smith; Robin Taylor; Richard I Cooper; Stephanie E Harris; A Guy Orpen
Journal:  J Chem Inf Comput Sci       Date:  2004 Nov-Dec

5.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

6.  Density-functional exchange-energy approximation with correct asymptotic behavior.

Authors: 
Journal:  Phys Rev A Gen Phys       Date:  1988-09-15

7.  Distinct interaction of human and guinea pig histamine H2-receptor with guanidine-type agonists.

Authors:  M T Kelley; T Bürckstümmer; K Wenzel-Seifert; S Dove; A Buschauer; R Seifert
Journal:  Mol Pharmacol       Date:  2001-12       Impact factor: 4.436

8.  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na(+)/H(+) exchanger.

Authors:  Didier Laeckmann; Françoise Rogister; Jean Victor Dejardin; Christelle Prosperi-Meys; Joseph Géczy; Jacques Delarge; Bernard Masereel
Journal:  Bioorg Med Chem       Date:  2002-06       Impact factor: 3.641

9.  4-Guanidinobenzene-sulfonic acid.

Authors:  Wei-Feng Wang; Chang-Mei Wei; Hong-Jun Zhu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-08

10.  8-Quinolylguanidinium chloride.

Authors:  Chang-Mei Wei
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-07
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