Abelsonite, nickel porphyrin` a new mineral from the .Green River

AmericanMineralogist, Volume63,pages930-937, 1978
nickelporphyrin'a newmineralfrom the
Abelsonite,
.Green
RiverFormation,Utah
CHnnI-rsMIlroN
TheGeorgeWashingtonUniuersity,Washington,D'C' 20052
and tl.S. GeologicalSuruey,Reston,Virginia22092
Eow,'rRPJ. DwonNlr
IJ.S.GeologicalSuruey,Reston,Virginia22092
PerntctnA. EsrnP-BnnNns
U.S. DePartmentof EnergY
. ltashington,D.C' 20545
Rosrnt B. FINxTI-ueN
L/.5.GeologicalSuruey,Reston,Virginia22092
Apoln Pessr
Departmentof Geologyand Geophysics
IJniuersi ty of Califurnia, Ber keIey, Califur nia 94720
It'tP S uS,o'NP,'rt-trlnR
Department
of Geology, Florida Atlantic
Boca Raton, Florida 33431
Uniuersity
Abstract
has
Abelsonite,a crystallinenickel porphyrin with the probablecompositionCa,HsrNoNi,
River
of
the
Green
shale
oil
Zone
Mahogany
the
near
in
or
drill
cores
eight
been found in
Formation in Uintah .County, Utah. Associatedauthigenicminerals include orthoclase'
pyrite, quartz, dolomite, anaicime,and a K-Fe micaceousmineral. Abelsoniteoccurs as
pink-purp.leto
algregatis of platy crystals,as much as 3 mm long, that rangein color from
to
a
semimetallic
Oait ieddish-brown.The crystalsarevery soft ((3 on Mohs scale)and have
reddishred
or
is
the
color
light
is (1Tl). In transmitted
luster.Probablicleavage
adamantine
liquids and its
brown, with intenseabsorptionto .-.ddith-b.own.Its reactionwith high-index
is triclinic,
Abelsonite
characteristics..
optical
of
prevented
determination
strong absorption
=
=
7'284'a
ll'12'c
8'44,b:
,pu.rlg.oupaspectP*, with celldimensions(Weissenberg),a
: 9 0 . 5 3 ' ,B : t t Z " l S , , ^ y - - 7 9 o 3 4 ' ; v o l u m e 6 l 3 . 8 A s , c a l c u l a t e d d e n s i t y ( f o r Z = l ) : 1 . 4 5 9 /
intensity'
cme.The five strongestlines of the X-ray powder pattern (d value i-n A, relative
(40) 012.
indices)are 10.9(100) 010, 3.77 (80) itl, t.St 1iO; tOO,5.79 (40) 1T0,3.14
Ultraviolet,visible,and infraredspectraindicatethat abelsoniteis a deoxophylloerythroetioThe mineralis namedin honor of PhilipH'
a chlorophyllderivative.
porphyrin,presumably
Washington'
of
Institution
Carnegie
President,
Abelson,
1969by LawrenceC. Trudell (Departmentof EnIntroduction
Researchcenter: Dor/Lnnc)
Abelsonite,a nickel PorPhYrinwith a probable ergy/LarumieEnergy
Oil ShaleCorporation
Western
the
from
was first obsirved in in a sample
compositionof CsrHs2N4Ni,
930
404X/ 78/09I o-0930$02.oo
Cf,O3
MILTON ET AL.: ABELSONITE
931
Table l. Locationsof coreholes
and abelsonite-bearing
samples
in southeastern
Uinta Basin,UintahCounty,Utah
V/elI No.
Location
IIVOSCO
MDA/
Lr,nV
Sec J6 T
flor{h
Quadranele
9SR20E
nf
lin
raa+\
Big Pack Mt. NE
2 5 0 8 . 2- 2 5 0 8 . 1 5
Agency Drar,v NE
2 2 2 . 9 2- 2 2 2 . 9 3 , 2 2 3 , 2 2 3 . 5 ) - 2 2 3 . 5 9 ,
226.p, 229.77
BatesKnoll-
65.26, r8I.I9, l-87.35 - r8I.37,
78L./+7, 782.17, 782.22, LgO.25,
19O.61, r%.7O, r9O.75 - r9O.9
Z
>eC
J)
?
.(aa
1ry T
d
Sec35T]-JSB22E
'
6
Sec31T13SR22E
|
7
Secl-dTI/+SR22E
Pine Sprirg
15.07 - 15.rO, 15.8 - 45.83
'r
8
Sec26T13SR23E
Cooper Carryon
98.61 - 98.68, rO2.18 - rO2.52
"
9
Sec6
Burnt
1 6 0 . 2 6- a 6 o . 2 7 , 2 3 2 . 2 , 2 5 r . 8 3 ,
2 5 3 . O 3- 2 5 3 . 2 , 2 5 4 . 3 5 , 2 5 1 . 1 1 ,
rr
I
vnnzIL
T3SR22
T1-3SR2/-E
E
86.05 - 86.l'0, 86.2 - 86.3, 196.3r,
t95.9r, 20r.6
r o 2 . 3 - \ o 2 . 5 , 2 3 1 . 6 0- 2 3 1 . 6 2
i l t l
Timber
test core (Table l, Wosco). He recordeda "tight
verticalfracturefrom 2508.4to 2508.8ft. with black
coatingsand occasionalfine pink-purplemetallic
patches"not over 3 mm in size(Trudell,1970).The
secondobservation(Table l, No. 3) was also reportedby Trudell(personalcommunication,
November 20, 1975)as "minute purplecrystallinemasses."
Soonthereafter,
Cassandra
Sever(Don/Lnnc) noted
that abelsonitewas found in six other cores,which
are listedin Tablel.
Abelsonite(approvedby the Commissionon New
Minerals and Mineral Names, IMA) is named in
honor of Philip H. Abelson,Presidentof the CarnegieInstitution of Washingtonand editor of Science,a pioneerin organicgeochemistry.
Specimens
of
type abelsonite(NMNH 143566)have beendeposited in the National Museum of Natural Historv.
Washington,
D.C.
Occurrenceand localities
In the eight localities(Table l), all in Uintah
County, northeasternUtah (Fig. I ), abelsoniteis
presentas macroscopically
crystallized
aggregates
of
platy crystals.All the sampleswerefound in or near
the Mahogany Zone, probably in the lower part
(W.B. Cashion,U.S. GeologicalSurvey,personal
communication,May ll, 1976).The Mahogany
Zoneis the subsurface
equivalentof the kerogen-rich
MahoganyLedgein the ParachuteCreekmemberof
the Green River Formation.Pink platy abelsonite
was found in one sample(Wosco; the type locality)
at a depth of 2508ft.; this localityis about l6 miles
(core samples
northwestof the other occurrences
were
hereindesignated
asDoElLERc),wheresamples
found at much shallowerdepths,lessthan 258 ft.
porphyrins
Until now, naturallyoccurringcrystalline
havenot beenrecognized,
althoughMoore and Dunning (1955)solvent-extracted
nickeland iron porphyrins from the eastward-extending
MahoganyLedge
oil shale in Colorado; and Sugiharaand McGee
(1957)isolated,by solventextraction,a nickelporphyrin from Utah gilsonite.The NW-SE trending
gilsoniteveins,as mappedby Cashion(1967),arc a
11f
11tr
ffi
10r
1F
Green
Rrw Fumaion ffi.Abelson1e oeruence
Fig. l. Map showingextentof GreenRiver Formationand area
in northeasternUtah.
of abelsoniteoccurrences
932
MILTON ET AL.: ABELSONITE
Fig. 2. Aggregateof abelsonitecrystalsfrom Dot/LEnc No. 6,
UintahCounty,Utah. Photomicrograph,
60 X.
few kilometers northeast and east of the abelsonite
type locality to dark reddish-brown at the other occurrences.The luster is semimetallicto adamantine.
Abelsonite does not fluorescein long- or short-wave
ultraviolet radiation.
Determination of indices of refraction by the immersion method was impossiblebecauseof the strong
reddish-brown to reddish-black absorption and because the mineral is rapidly attacked by diiodomethane and other high-index liquids. Abelsonite is insoluble in water and in dilute hydrochloric and nitric
acids; it is soluble in benzeneand acetone.
The mineral is very soft ((3 on Mohs scale) and
easily deformed by pressure. Probable cleavage is
( l T l ) . T h e d e n s i t y o f a b e l s o n i t e ,1 . 4 5 g / c m 3 , w a s
c o m p u t e du s i n gt h e X - r a y c e l l v o l u m e ( 6 1 3 . 8A 3 ) a n d
the mass-spectrometricmolecular weight (518), assuming one molecule per unit cell. During an experiment, a particle was observedto sink in dichloromet h a n e ( G : 1 . 3 3 )a n d f l o a t i n c h l o r o f o r m ( G : 1 . 4 8 ) ;
the calculateddensityis within the range of the experimental observations.
localities.
Becauseof the rarity and small size of the abelsonite crystal aggregates,ranging from 30 micrometers
to 3 mm (Fig. 2), and superficialresemblanceto "iron
stains" or similar nondescript material, abelsonite
Chemical analysis
may easily be overlooked in casual observation. Its
identification in at least seven of ten Doe/Lrnc
Microprobe analysisof six separategrains of type
cores,from test holes scatteredover an area ofabout
abelsoniteshowed a range in nickel content from ll
250 squaremiles, and in the Wosco core (from a test
hole about 16 miles northwestof the others),indicates
that the mineral probably is presentin a fairly extensive area in the Green River Formation.
The "black coatings," noted above by Trudell
(shown in Figs. 3, 4, and 5), are a finely crystallized
dark-brown micaceousaggregate,not noted in previous Green River mineralogical investigations;its
precise nature is not known. Preliminary study suggests a K-Fe mica-like mineral. Other identifiable
authigenic minerals associatedwith abelsonite are
albite and orthoclase (Figs. 3, 4, and 5), pyrite,
quartz, dolomite, and analcime.
The descriptivedata of this report, particularly the
unit cell determination by Adolf Pabst, and the infrared, visible, ultraviolet, and mass spectrometric
studiesby P.A. Estep-Barnesand SusanPalmer,were
made on the type material (Wosco). Identification of
abelsonitefrom the sevenDor,/Lrnc cores is based
on comparison of their X-ray powder patterns and
physical properties,ultraviolet and massspectra,and
on the presenceof nickel as the only metal ion.
Physical properties
Abelsonite occurs as small (<3 mm) aggregatesof
thin translucent laths or plates (Fig. 2). Its color
variesfrom light "pink-purple" (Trudell, 1970)at the
F i g 3 . L a r g e ( b r o k e n ) c r y s t a l o f a b e l s o n i t e( a ) , w i t h s h e a v e so f
a n a u t h i g e n i c m i c a c e o u sm i n e r a l ( m ) , a n d o r t h o c l a s ec r y s t a l s( o )
( W o s c o ) . S c a n n i n ge l e c t r o n m i c r o g r a p h , 1 6 0 X
MILTON ET AL.: ABELSONITE
933
to l4 percent.Approximately l0 fragmentsfrom the
other occurrenceswere observedby using a scanning
electron microscope equipped with an energy-dispersivesystem;the nickel content was estimatedto be
about 10 weight percent. In addition to the nickel
determination,carbon valuesof 40-50 weight percent
were obtained by microprobe analysis on the type
material. Nitrogen could not be determined and
probably was below the level of detection for the
microprobe system (-10 weight percent). No other
elementswere detected.The intimate intergrowth of
m u c h o f t h e a b e l s o n i t ew i t h o t h e r m i n e r a l s( F i g s .3 , 4 ,
and 5) and the limited quantity available(a few milligrams) made attempts at more detailed chemical
analysisimpractical.
X-ray crystallography
Four fragments of type abelsonitewere examined
by single-crystalX-ray diffraction methods.Only two
of them yielded useful results. Altogether, no more
than a few score of distinct identifiable diffraction
spots extend to sindltr : 0.3. This limited range of
"reflection," similar to that reported for a related
compound, Ni-etioporphyrin (Crute, 1959;Fleischer,
1963), for which disorder has been postulated, is
probably also attributable to disorderor other crystal
imoerfections.
F i g . 4 . A b e l s o n i t e ( a ) w i t h a u t h i g e n i c orthoclase (o) and
mlcaceous
m i n e r a l ( m ) ( W o s c o ) . S c a n n i n gelectron micrograph,
800 x.
Fig. 5 Unidentified micaceous mineral with orthoclase crystals
( o ) ( W o s c o ) S c a n n i n ge l e c t r o n m i c r o g r a p h , 6 0 0 X .
The lattice derived from Weissenbergdata is triclinic with diffraction aspectP*. From measurements
on a [0T] rotation pattern and the correlated0-, lst-,
2nd- and 3rd-layer equi-inclinationWeissenbergpatterns, the reciprocal lattice constants(scaledto tr =
I .54178A)were determinedand the direct latticeconstants calculatedfrom these.The cell as reported in
Table 2 is "reduced" in the sensethat a, b and c are
the shortest non-coplanar translations; it is righthanded and conforms to "rule 6" of Crystal Data
(Donnay et al., p. 2, 1963), "non-acute interedge
anglesa and 8." This correspondsto Buerger'sType
I crystal, orientation abc : XYZ (Buerger, 1963).
The lattice dimensions refined by Dr. Daniel Appleman by least-squaresanalysisof the powder data
(indexed with the aid of single-crystalWeissenberg
photographs) are listed in Table 2 for comparison
with those derived from Weissenbergdata.
The orientation of the translation lattice with respectto the outline of a typical lath is partly shown in
Figure 6. The plane of the lath (or cleavage)( I I I ) has
a calculatedd spacingof 3.76A. There are 2l lattice
planeswith larger spacings.The axis of elongation,as
observedon only two fragments,is [01], with ident i t y d i s t a n c ec a . l 3 . l 8 A . T h i s i s s o m e w h a tu n u s u a l ,a s
the cleavageplane of micaceouscrystalsis generally
that of greatestspacing,and the longest axis is ordinarily normal or nearly normal to the cleavage.
934
MILTON ET AL.: ABELSONITE
Table 2. Cell constants of abelsonite
fYm
a
s./r1R
least squares refinment
of Dwder data
8.t08(21) f
b
11 .12
Lr,185(27 )
c
n)A
7.299(!r)
900r,
tt3o 45,
,{
v
7f34'
Table 3. X-ray powderdiffractiondata for type abelsonite
(Wosco)
-vergsrglcq
hkl,
olseneal)
E (8)2)
s(8)
r
010
10.91
100
7.58
7.63
110
6.41
6.85
5
9oo5r(15 ) '
001
6.65
6.63
30
11/+oO8(12
)|
r01
6.17
79o1903)'
6D.8 R3
r0,9
100
50
011
111
110
011
020
5.73
5,79
/,0
5 5t
?5
5,16
11r
5.31
The numberof parametersrequiredto specifyall
L20
t0
1.90
atomic positionsfar exceeds
the numberof observ021
r0
1.36
1.)9
able reflections,even if the crystalsshould contain
101
4.22
111
but a singletype of molecule.A full crystal-structure
021
1.09
determinationof abelsoniteis not possibleat this
120
1.U7
time.
2Ll
1.0'
Nevertheless,
the meagercrystallographic
data ob2IO
3.8r
tainedfor abelsonite
do givea basisfor somespecula200
3.79
tions about the structure.From latticedimensions
111
80
3'76
3,77
220
3.11
alone,therebeing but one Ni per cell, it is easyto
2LO
show that distancesfrom a Ni atom to the nearest
QO
eightNi atomsarea 7.30,c 8.51,[01] 8.66,and b
02
3.21
ll.l8A, eachtwo times,average
8.91A.In the struc3 '2/'
ture of nickeletioporphyrin-I(Fleischer,1963),with
012
),r1
10
a densityof 1.35g/cms,distances
from a Ni atom to
2.60
5
2.29
5
the nearest8 Ni atomsarej.93A for four and 12.04A
2.27
5
for four, average9.984; the moleculesare nearly
Indexed with the aid of sirgle-crystal
Weissenberg photogrcphs.
planarand arein a staggered
arrangement
by 4, axes I)2) Calculated
(tatte
fr@ singtecrystal
Weiss$berg
cel1 constdts
Z).
m Deb_yescherrer powaler cmera.
V-filtered
CrK rediation
with about 3.lA betweenthe levelsof the molecules. 3) I]1.59
(\ = 2.289624).
No lnterml
stddard.
Intensities
visully
estrlmted.
The molecules
in abelsonite,
if parallelto (lTl), are
staggered
in a lesssymmetrical
mannerwith a greater
distancebetweensuccessive
levels.The meshareaof
(l I l) in abelsonite
suggesting
that
is 162.8A',whereas
that of (001) in nickeletioporphyrin-Iis 213.4A2,
the moleculesin abelsonitemay departmore from
planarity,which correlateswith the slightlygreater
densityof abelsonite.The mineralsurelyformed at
depth under far greaterpressurethan the synthetic
material.
Indexed X-ray powder diffraction data for type
abelsonite(Wosco) are given in Table 3. Powder
patternstaken of materialfrom the other localities
werevirtuallyidentical.
? t?
Fig. 6. Idealized sketch of orientation relations in abelsonite.
The (lTl ) surfacesare always buckled; the [0T] edge was observed
as a straight line on only one fragment, and transversesurfacesare
uneven though there is a suggestion of faces parallel to this edge
and at a large angle to the cleavage.
Ultraviolet-visible spectrophotometry,
massand
infrared spectrometry
Experimentalp rocedure
Small amounts of abelsonitecrystalswere dissolvedin benzene
in acetone,and UV-visiblespectra
93s
MILTON ET AL,: ABELSONITE
28,000
26,000
FREQUENCy,
cm-l
24,000
22,ooo
20,000
18,000
equippedwith a direct probe inlet system.The probe
were 205oand 275oC,reand sourcetemperatures
spectively.
UV-uisibleand massspectrometricresults
The UV-visible spectraobtainedon fragmentsof
z
abelsonitefrom two samples(Wosco and DoE/
Lnnc) werethat of a porphyrin(Falk, 1964)having
spectralbandsat 392, 5lO, and 550 nm in benzene
( F i g . 7 ) a n d 3 9 0 , 5 1 2 a, n d 5 5 2n m i n a c e t o n eT.h e
data suggestthat abelsoniteis a deoxophylloerythroetioporphyrin-type(DPEP) porphyrin with an
of a smallpeakat 618nm
isocyclicring.The presence
from the
spectrum
of abelsonite
in the acetonevisible
Fig. 7. UV-visibleabsorption
spectrum
(in
of type abelsonite
14
presence
about
of
the
Wosco samplesuggested
benzene
solution;curvesrepresent
two different
dilutions).
percent(of total pigment)free-baseporphyrin.Howrecorded using a Beckmanl Acta CIII and a Perkin- ever, only the 618-nm band was observed;other
were obscuredby
Elmer Model 350 scanning spectrophotometer.The bands of the free-baseporphyrin
at
and 552nm.
bands
512
metalloporphyrin
the
infrared spectral data were obtained on a 30 pg
(1967)
that X-ray
have
shown
Donnay
and
Storm
sample using infrared microsampling techniquesdeof the isopatterns
end-members
powder
even
the
of
scribedby Estepet al. (1973).Micropelletswere scan(TTP) and
porphyrin
tetraphenyl
morphous
series
ned on a Perkin-Elmer Model 2l prism spectropho(AgTTP), the free-base
tometer (2-15 m) and a Perkin-Elmer Model 621 silver tetraphenylporphyrin
River porphyrinand
of
the
Green
analogs
and
silver
grating spectrophotometer (5000-200 cm-1), both
Thus, abelporphyrin,
indistinguishable.
are
nickel
equipped with reflecting type 6X ultra-micro beam
non-stoichiometric
a
thought
of
as
may
best
be
sonite
condensers.Mass spectrometricanalyseswere made
using a Dupont 491-BR mass spectrophotometer compound.
(Fig.8) of an abelsonanalyses
Massspectrometric
I E q u i p m e n t n a m e d i n t h i s r e p o r t i s f o r i d e n t i f i c a t i o no n l y
showed
that the major
70eV
recorded
at
ite
sample
and
(m/e) peak was 518 and a secondary
d o e s n o t n e c e s s a r i l yi m p l y e n d o r s e m e n t .
mass/charge
I
5$
520
5r0
5m
Fig. 8. Partial l2 ev massspectrumof abelsonitefrom GreenRiver Formation,Utah.
936
MILTON ET AL.: ABELSONITE
,,"'\
The molecularweightof 518 indicatesthat this
nickel porphyrinhas 3l carbonsand not 32 as was
suggested
earlier(Pabstet al., 1975).The empirical
formula for abelsoniteshouldthen be Cg,HazNnNi;
the calculated
compositionfor C'HrrNoNi (in weight
percent)is: C 72.33,H 6.07,N 10.55,Ni 11.05.A
proposedmolecularstructurefor abelsonite
is shown
in Figure9. It is not possible,
at present,to presenta
more specificmolecularstructure.
-"
\:\/.:2
Infrared spectrometry results
The general characteristicsof the infrared spectrum appearin Figure 10,curveb (obtainedon the
prism instrument).Frequencies
for C-H stretching
vibrations,which werewell resolvedinto threecomm/e peakwasat 520.Theratio of the 518to 520mass ponents(2970,2915,2860cm-') in the gratingspecspectralpeak intensitiesroughlycorresponds
to the trum, suggesta predominance
of aliphaticgroupsin
natural abundanceof the two major stableisotopes the structure.The absenceof a strong absorption
of nickel(Niu' : 67.8percentand Ni6o: 26.2 per- band in the C : O stretchingregionof 1780-1630
cent).
cm-r indicatesthat thereare no carbonylgroupsin
Fig. 9. Proposed molecular structure of abelsonite, C'HrrNoNi;
nickel
8-desmethyldeoxophylloerthyroetioporphyrin.
Roman
numerals I-IV are cyclic tetrapyrrole rings; V is a cycloalkane ring.
ar-I
FREQUENCY
t
I
-z
$ ri iitr
=
z
W A V E L E N G Tp
Hn,
FREQUENCY,6m-1
5,000
| , |
3,000
,
i,,',1,'
2,000
, ' | , |
1,500
|
,
r,200
1,000
I
900
800
1,,,,t,,1
I
I
U
6
z.
4Y
F
F
s
=
z
F
\n/rl
vv 1r
it
\-r
n/
2)
17
"
I
\
2
S = aS I L I C A T E
10
ll
IZ
13
T4
l3
WAVELENGTH
,
rm
Fig. 10.Infraredabsorptionspectraof nickel-porphyrin
(a) Nickel-etioporphyrin
complexes.
I (synthetic
API No. 1906,nujoland
fluorolubmulls);(b) Abelsonite(Wosco,CsI micropellet).
937
MILTON ET AL.: ABELSONITE
the structure. Additional absorption bands in the
low-frequency mid-infrared region of the spectrum
were observedat 620(w : weak) 602 (w) 535 (w) 512
(w) 441 (s : strong) and 392 (w) cm-l. Absorption
b a n d sa t 3 4 3 0( m : m e d i u m ) 1 6 3 5( w ) , 9 9 5 ( w ) c m - 1
(labeled"S" in Fig. 10, curve b) and at 440 cm-1 (s)
(observedin the grating spectrum)matched well with
the major absorption bands in the spectrumobtained
for the fine-grained black material that abundantly
coated the surface of the host rock. A microscopic
examination of the three translucent grains of abelsonite used to obtain the infrared spectrum showed
several occluded black specks.The spectrum of the
black material isolated from the host rock indicates
that it is an hydroxyl-containing layer silicate (presumably the "micaceousmineral" referredto above).
Since the infrared spectrum of a nickel desmethyl
DPEP was not availablefrom the literature for comparison with that of abelsonite, a comparison was
made with that of nickel-etioporphyrin I (Fig. 10,
curve a, American Petroleum Institute, 1957).There
are gross overall similar spectral characteristics,but
minor differencesindicate a different structure, as
was verified by UV-visible and mass spectraldata.
Acknowledgments
Wearegratefulto Lawrence
C. Trudell,Dor/LEnc,for bringing
this unusualmineralto our attention.
We wouldalsolike to
expressour appreciationfor assistance
to the followingcolleagues
at the U.S.Geological
Survey:Mary E. Mrose,MichaelFleischer,
Irving Breger,W B. Cashion,and JamesLindsay;alsoto Daniel
Appleman,Smithsonian
Institution,Washington,
D.C.;to Professor Carlyle B. Storm, Howard University;to Dr. Akira Kato,
National ScienceMuseum,Tokyo; to Dr. Virgil L. Goedken,
FloridaStateUniversity,Tallahassee;
and to Dr. Earl W. Baker,
Florida Atlantic University,for aid in interpretingthe massspectrometricdata and useof the Dupont491 BR massspectrometer
and BeckmanActa C I I I spectrophotometer
in his laboratory.
This investigation
wassupportedby NSF grantT4-13319.
References
AmericanPetroleumInstitute(1957)Selectedualuesof properties
of hydrocarbonsand related compounds.Category B. Infrared
serialnos.1906,1907,1908.
spectraldala Loose-leafdatasheets,
ResearchProject44.
Wiley, New
Buerger,M. J. (1963)ElementaryCrystallography.
York.
Cashion,W. B. (1967)Geology and fuel resourcesof the Green
Uinta Basin,Utah and ColoRiver Formation,southeastern
rado. U.S Geol.Suru.Prof. Pap.548.
Crute,M. B. (1959)The crystalstructureof nickeletioporphyrin
lI. Acta Crystallogr.,12, 24-28.
Donnay,J D. H., G. Donnay,E. G. Cox, O. Kennardand M' V.
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