There is an answer to your question find the pair of words that never appear together, and have the highest individual frequency (the sum of them):
Using the Penn Treebank as a text corpus, the top 10 pairs are:
(8090, 'the', 'the'),
(6364, 'the', 'of'),
(6209, 'the', 'to'),
(5923, 'the', 'a'),
(5923, 'a', 'the'),
(5617, 'the', 'in'),
(5556, 'the', 'and'),
(5168, 'the', '*-1'),
(5168, '*-1', 'the'),
(5144, 'the', '0')
The result should be quite intuitive.
Code:
import nltk, string
from collections import Counter, defaultdict
nltk.download('punkt')
nltk.download('ptb')
tokens = nltk.corpus.treebank.words()
ct = Counter(tokens)
tokens_high_freq = [x for x in ct if ct[x]>10 ]
bigrams = nltk.bigrams(tokens)
bigram_dict = defaultdict(list)
for a,b in bigrams:
bigram_dict[a].append(b)
bigrams_never = [(ct[a]+ct[b],a,b) for a in tokens_high_freq for b in tokens_high_freq
if b not in bigram_dict[a] and a not in string.punctuation and b not in string.punctuation]
print(sorted(bigrams_never, reverse=True)[:10])
-- Edit --
Corrected a coding mistake, thanks to @FrédéricGrosshans.